cas 80-54-6, Lily aldehyde | Articles data

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Preparation method of high-quality para-lilial
The invention provides a preparation method of para-lilial. High-quality para-lilial is synthesized by using p-tert-butyl benzene halide and methacrylic acid as raw materials in the presence of a catalyst. The raw materials and the solvent used in the method are low in cost, the coupling reaction of tert-butyl benzene halide and methacrylic acid can be efficiently carried out under the action of the catalyst, expensive and complex catalyst ligands do not need to be used, and the manufacturing cost is greatly reduced. Besides, the purification process in the production process can effectively remove isomer impurities, the hydrogenation process is high in selectivity, a high-quality para-lilial product can be obtained, the process is simple and easy to control, and industrial production is facilitated.
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(2020/06/30)

Carbonylative Transformation of Allylarenes with CO Surrogates: Tunable Synthesis of 4-Arylbutanoic Acids, 2-Arylbutanoic Acids, and 4-Arylbutanals
In this Communication, procedures for the selective synthesis of 4-arylbutanoic acids, 2-arylbutanoic acids, and 4-arylbutanals from the same allylbenzenes have been developed. With formic acid or TFBen as the CO surrogate, reactions proceed selectively and effectively under carbon monoxide gas-free conditions.
Wu, Fu-Peng,Li, Da,Peng, Jin-Bao,Wu, Xiao-Feng
p. 5699 - 5703
(2019/08/01)

Lily aldehyde preparation method
The invention discloses a lily aldehyde preparation method. Specifically, the lily aldehyde preparation method comprises the steps: (a) in an inert solvent and under existence of a catalyst and ligand, performing hydroformylation on compound shown by a formula II with hydrogen and carbon monoxide to form compound shown by a formula I. By means of the preparation method disclosed by the invention,high-purity lily aldehyde can be obtained, lily aldehyde production cost is reduced, and a production technology is simplified; furthermore, the preparation method is suitable for large-scale industrial production; thus, the preparation method has application value.
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Paragraph 0039; 0040; 0044

(2018/04/03)

A synthetic route to 4-alkyl-α-methylhydrocinnamylaldehydes
The 4-Alkyl-α-methylhydrocinnamylaldehydes (alkyl-isopropyl, isobutyl, methyl) are frequently used fragrances with desired floral (lilac, cyclamen, lily-of-the-valley) scent. These substances are valued for their good stability in basic solution and, therefore, are frequently used in soaps, detergents, or shampoos. These substances are synthesized by a two-step synthesis involving base catalyzed aldol condensation of 4-alkylbenzaldehyde with propanal followed by selective hydrogenation of the C=C bond. In aldol condensation, selectivity is decreased by formation of undesired products of propanal autocondensation 2-methylpent-2-enal. In this work the reaction conditions for homogenous catalyzed aldol condensation of 4-isobutylbenzadehyde with propanal were tested (catalyst type and amount, molar ratio of reactants, solvent type). Reaction conditions giving the best results (92% conversion, 79% selectivity) were adapted to other 4-alkyl-α-methylcinnamylaldehydes preparation with similar results. In the second step—hydrogenation of aldol product different types of catalyst (nickel, cobalt, palladium or Adkins catalyst), and also different solvents, were tested. Hydrogenation conditions leading to the highest yield (72% selectivity at 95% conversion) were adapted to other 4-alkylhydrocinnamyladehydes with similar results.
Vrbková, Eva,Vysko?ilová, Eli?ka,Rott, Martin,Zapletal, Martin,?erveny, Libor
p. 2603 - 2613
(2017/03/22)

Preparation method of lily aldehyde
The invention provides a preparation method of lily aldehyde. The method comprises steps as follows: tert-butylbenzene, a solvent and a catalyst are combined and stirred and mixed at a certain temperature; the solvent is any one of dichloromethane, chloroform, nitrobenzene and 1,2-dichloroethane; the catalyst is composition of Lewis acid and an acidic substance providing protons; the certain temperature ranges from subzero 60 DEG C to 40 DEG C; 2-methacrylaldehyde is dropwise added after mixing, and the mixture is kept at the constant temperature continuously after 2-methacrylaldehyde is dropwise added; 2-methacrylaldehyde is dropwise added for 2.5-3.5 h. By means of the method, the yield of lily aldehyde is high and can reach 50%-73%; the recovery rates of the solvent and tert-butylbenzene are high, the cost is saved, and the recovery rate of the solvent is 95%-98% while the recovery rate of tert-butylbenzene is 93%-98%.
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Paragraph 0026; 0027; 0028; 0029; 0030; 0031; 0032-0044

(2017/07/19)

An efficient TiCl4-catalysed method for the synthesis of para-substituted aromatic aldehydes
An efficient and highly selective synthesis of para-substituted aromatic aldehydes has been achieved by TiCl4-catalysed Friedel-Crafts alkylation of monosubstituted benzenes with methacrolein diacetyl acetal.
Zhou, Chenfeng,Su, Weike
p. 555 - 557
(2015/11/27)

A highly stereoselective organocatalytic approach to Lilial and muguesia
The stereoselective alkylation of aldehydes with benzodithiolylium tetrafluoborate gave a straightforward access to key compounds for the synthesis of fragrances and flavors. Georg Thieme Verlag Stuttgart · New York.
Gualandi, Andrea,Emma, Marcogiuseppe,Giacoboni, Jessica,Mengozzi, Luca,Cozzi, Piergiorgio
p. 449 - 452
(2013/04/10)

Chemoselective hydrogenation of α,β-unsaturated aldehydes with modified Pd/C catalyst
Selective hydrogenation of α,β-unsaturated aldehydes with modified Pd/C catalyst was developed. The reduction of CO bond could be efficiently inhibited by the addition of carbonates, and high selectivity to the corresponding saturated aldehydes was achieved under mild conditions. This protocol provides an alternative for efficient preparation of saturated aldehydes.
Du, Wen Qiang,Rong, Ze Ming,Liang, Yan,Wang, Yong,Lu, Xin Yi,Wang, Yi Fan,Lu, Lian Hai
experimental part
p. 773 - 776
(2012/08/14)

An asymmetric hydroformylation catalyst that delivers branched aldehydes from alkyl alkenes
Surprising selectivity: The first enantioselective hydroformylations of simple alkenes of type RCH2CH=CH2 to preferentially deliver the branched aldehyde product have been discovered using a new chiral ligand, named bobphos (see scheme). Established ligands are unselective in this reaction or show a slight preference towards the linear aldehyde. Copyright
Noonan, Gary M.,Fuentes, Jose A.,Cobley, Christopher J.,Clarke, Matthew L.
supporting information; experimental part
p. 2477 - 2480
(2012/04/18)

Process for Producing Aromatic Aldehyde Compound
A process for producing an aromatic aldehyde compound has steps of converting alkyl-substituted or non-substituted benzene into a compound of formula I by halomethylation, and allowing the compound of formula I and alkyl aldehyde to react in presence of phase transfer catalyst at a reaction temperature under alkaline condition to obtain the aromatic aldehyde compound.
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(2012/10/23)

Phase Transfer Catalyst for Producing Aromatic Aldehyde Compound
Provided is a phase transfer catalyst for producing an aromatic aldehyde compound, comprising a compound of formula I, wherein R1 is hydrogen, methyl, ethyl, isopropyl, isobutyl or tertbutyl; R4, R5 and R6 are independently selected from alkyl groups containing 1 to 6 carbon atoms; and X is fluorine, chlorine, bromine or iodine.
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Page/Page column 4

(2012/10/23)

Acid promoted CIDT for the deracemization of dihydrocinnamic aldehydes with Betti's base
Racemic α-epimerizable and unfunctionalized aldehydes have been converted into enantiomerically enriched mixtures through a sequence of (i) a conversion into the diastereoisomeric 3-substituted 1-phenyl-2,3-dihydro-1H- naphtho[1,2-e][1,3]oxazines by reaction with the (R)- or (S)-1-(α- aminobenzyl)-2-naphthol (Betti's base), (ii) an acid promoted crystallization-induced diastereoisomer transformation (CIDT), and (iii) a clean cleavage of the dihydro-1,3-naphthoxazinic ring of the enriched diastereoisomer, easily collected by filtration, allowing the recovery of the enantiomerically enriched aldehydes and the chiral auxiliary.
Rosini, Goffredo,Paolucci, Claudio,Boschi, Francesca,Marotta, Emanuela,Righi, Paolo,Tozzi, Francesco
experimental part
p. 1747 - 1757
(2011/02/28)

Functionalised ionic liquids: Synthesis of ionic liquids with tethered basic groups and their use in Heck and Knoevenagel reactions
A simple and efficient synthesis of a novel series of ionic liquids bearing nucleophilic (Me2N) and non-nucleophilic base (iPr 2N) functionalities is described. The non-nucleophilic base functionality resembles the structure of the Huenig's base (N,N-diisopropylethylamine), which has been used widely in organic synthesis. A qualitative measure of the basicity of these ionic liquids is presented by utilising their interaction with universal indicator. The basicity of these ionic liquids was found to be dependent on the amine tether and choice of linker between the two nitrogen centres. The relative base strength of these ionic liquids was also probed by using them as catalysts in the Heck and Knoevenagel reactions. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
Forsyth, Stewart A.,Froehlich, Ute,Goodrich, Peter,Gunaratne, H. Q. Nimal,Hardacre, Christopher,McKeown, Angela,Seddon, Kenneth R.
experimental part
p. 723 - 731
(2010/06/17)

Bioreduction of α-methylcinnamaldehyde derivatives: Chemo-enzymatic asymmetric synthesis of Lilial and Helional
Nonracemic aryl-substituted α-methyldihydrocinnamaldehyde derivatives employed as olfactory principles in perfumes (Lilial, Helional) were obtained via enzymatic reduction of the corresponding cinnamaldehyde precursors using cloned and overexpressed ene-reductases. (R)-Enantiomers were obtained using the old-yellow-enzyme (OYE) homolog YqjM from Bacillus subtilis and 12-oxophytodienoic acid reductase isoenzyme OPR1 from tomato (e.e. max 53%), and (S)-aldehydes were furnished in up to 97% e.e. using isoenzyme OPR3, nicotinamide 2-cyclohexene-1-one reductase NCR from Zymomonas mobilis and yeast OYE isoenzymes 1-3 under optimised reaction conditions in the presence of t-butyl methyl ether as the co-solvent. The stereochemical outcome of the reduction of α-methylcinnamaldehyde using NCR and OYEs 1-3 [previously reported to be (R)] was unambiguously corrected to be (S).
Stueckler, Clemens,Mueller, Nicole J.,Winkler, Christoph K.,Glueck, Silvia M.,Gruber, Karl,Steinkellner, Georg,Faber, Kurt
supporting information; experimental part
p. 8472 - 8476
(2011/01/10)

PROCESS FOR CONTINUOUS HYDROGENATION OR HYDROGENATING AMINATION
A process is described for continuously hydrogenating unsaturated compounds, in which particles of a first hydrogenation catalyst are suspended in a liquid phase in which an unsaturated compound is dissolved, the liquid phase, in the presence of a hydrogenous gas at a first partial hydrogen pressure and at a first temperature, is conducted through a packed bubble column reactor in cocurrent counter to the direction of gravity, the effluent from the bubble column reactor is sent to a gas-liquid separation, the liquid phase is sent to a crossfiltration to obtain a retentate and a filtrate, the retentate is recycled into the bubble column reactor and the filtrate, in the presence of a hydrogenous gas at a second partial hydrogen pressure and at a second temperature, is passed over a bed of a second hydrogenation catalyst, wherein the second partial hydrogen pressure is at least 10 bar higher than the first partial hydrogen pressure.
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Page/Page column 5

(2010/04/25)

Arylation of β-methallyl alcohol catalyzed by Pd(OAc)2 in combination with P(t-Bu)3: application to fragrance synthesis
Pd(OAc)2 in combination with P(t-Bu)3 catalyzes the coupling of β-methallyl alcohol with 1-bromo-3,4-(methylenedioxy)benzene (1a), 1-bromo-4-methoxybenzene (1b), or 1-bromo-4-tert-butylbenzene (1c). The reaction affords the corresponding 2-methyl-3-aryl-propanals, which are valuable floral fragrances. With 1a or 1b high reaction rates are obtained at 130 °C using NMP/water mixtures and an inorganic base such as Na2CO3. The chemoselectivity of the reaction is almost complete, so that the process appears practically feasible. In contrast, the coupling of β-methallyl alcohol with 1c proceeds with low reaction rates.
Scrivanti, Alberto,Bertoldini, Matteo,Beghetto, Valentina,Matteoli, Ugo
p. 543 - 548
(2008/09/16)

Arylation of allyl alcohols in organic and aqueous media catalyzed by oxime-derived palladacycles: Synthesis of β-arylated carbonyl compounds
A 4-hydroxyacetophenone oxime-derived palladacycle catalyzes the Mizoroki-Heck reaction of allyl alcohols with aryl iodides, bromides, and chlorides in aqueous and organic solvents. The reaction takes place in the presence of dicyclohexylmethylamine or cesium carbonate as bases, the addition of tetrabutylammonium bromide (TBAB) as additive for aryl bromides and chlorides being necessary. Under these reaction conditions, β-arylated aldehydes and ketones are mainly obtained using a rather low loading of palladium (0.1-1 mol%). Similar catalytic activity is shown by a Kaiser oxime resin-derived palladacycle, which allows one to perform recycling and reusing experiments with low Pd leaching. The high regio- and chemoselectivity observed supported that these palladacycles, working as a source of Pd(0) species, operates mainly through a neutral mechanism. This methodology has been applied to the synthesis of important β-arylated carbonyl compounds, such as 4-phenylbutan-2-one, 4-(4-hydroxyphenyl)butan-2-one, dihydrochalcones, the anti-inflamatory nabumetone, and the fragance β-lilial. γ-Arylation is observed in the reactions of allyl alcohol and but-3-en-2-ol with 2-iodoaniline giving mainly the corresponding quinolines. The same tendency is observed in the case of 1,1-dimethylallyl alcohol affording either γ-arylated alcohols or (E)-1-arylisoprenes.
Alacid, Emilio,Najera, Carmen
p. 2572 - 2584
(2008/09/19)

Applied photochemistry - Light controlled perfume release
Ambient light is one of the most suitable available trigger conditions for the release of covalently bound volatile odorants in home- and laundry-care applications. We report on three complementary classes of light-cleavable fragrance precursors, covering the controlled release of odorants with a wide range of functional groups. o-Hydroxy cinnamates 1 undergo a UV-induced double bond isomerization followed by transesterification to release coumarin and a fragrance alcohol of choice. α-Alkoxyacetophenones 10 and α,α-dialkoxyacetophenones 12 undergo Norrish type II fragmentations upon UV-irradiation, thereby releasing one or two equivalents of fragrant aldehydes, respectively. Finally, photoexcited Xanthenoic esters 22 undergo fragmentation to release reactive acyl radicals, which further cyclize onto internal olefins to form perfumery lactones of various ring sizes. Schweizerische Chemische Gesellschaft.
Derrer, Samuel,Flachsmann, Felix,Plessis, Caroline,Stang, Melanie
p. 665 - 669
(2008/03/13)

Controlled light-induced release of volatile aldehydes and ketones by photofragmentation of 2-oxo-(2-phenyl)acetates
The light-induced controlled release of fragrances from photolabile 2-oxo-(2-phenyl)acetates via Norrish Type II photofragmentation was evaluated by irradiation of the precursors in different solvents and on cotton in a typical fabric softener application. The desired photooxidation was found to work efficiently in water-based systems, and it tolerates the presence of oxygen. The formation of a certain amount of alcohol besides the desired aldehyde or ketone was attributed to further reaction of the photochemically released carbonyl compound, rather than to ester hydrolysis in an aqueous environment. Schweizerische Chemische Gesellschaft.
Levrand, Barbara,Herrmann, Andreas
p. 661 - 664
(2008/03/11)

One-pot multistep synthetic strategies for the production of fenpropimorph using an ionic liquid solvent
The one-pot synthesis of the fungicide fenpropimorph has been achieved using two different synthetic strategies in an ionic liquid. The first pathway consists of a Heck coupling followed by reductive animation; the second pathway consists of an aldol condensation followed by hydrogenation/reductive animation. Homogeneous and heterogeneous palladium catalysts have been utilised in the ionic liquid to provide a catalyst/solvent system that is suitable for recycling and process optimisation.
Forsyth, Stewart A.,Gunaratne, H. Q. Nimal,Hardacre, Christopher,McKeown, Angela,Rooney, David W.
p. 94 - 102
(2012/12/21)

Oxidative coupling of benzenes with α,β-unsaturated aldehydes by the Pd(OAc)2/molybdovanadophosphoric acid/O2 system
The oxidative coupling reaction of benzene with an α,β- unsaturated aldehyde was examined by the combined catalytic system of Pd(OAc)2 with molybdovanadophosphoric acid (HPMoV) under atmospheric dioxygen. Thus, the reaction of benzene with acrolein under dioxygen (1 atm) by the use of catalytic amounts of Pd(OAc)2 and H4PMo 11VO40·26H2O in the presence of dibenzoylmethane as a ligand in propionic acid at 90 °C for 1.5 h afforded cinnamaldehyde in 59% yield and β-phenylcinnamaldehyde in 5% yield. This catalytic system was extended to the direct oxidative coupling through the C-H bond activation of various arenes with acrolein and methacrolein.
Yamada, Tomoyuki,Sakaguchi, Satoshi,Ishii, Yasutaka
p. 5471 - 5474
(2008/04/18)

CONTINUOUS METHOD FOR PRODUCTION OF CINNAMALDEHYDE AND DIHYDROCINNAMALDEHYDE DERIVATIVES
The present invention relates to a continuous process for the preparation of cinnamaldehyde or cinnamaldehyde derivatives by continuous reaction of benzaldehyde derivatives with alkanals in the presence of bases and optionally subsequent continuous hydrogenation in a circulation reactor in the presence of a suspension catalyst and hydrogen to give dihydrocinnamaldehyde derivatives.
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Page/Page column 9

(2008/06/13)

Functional fragrance precursor
The present invention relates to a class of fragrance precursor compounds comprising one or more of the compounds derived from the reaction of X—OH and an aldehyde or ketone, said fragrance precursor compounds being of the formula X—O—C(R) (R*) (OR**) wherein R is a C6-24 alkyl group, a C6-24 aralkyl group or a C6-24 alkaryl group; R* is H or a C6-24 alkyl group, a C6-24 aralkyl group or a C6-24 alkaryl group; R** is H or X; X—O representing a moiety derived from X—OH, and wherein X—OH is a compound selected from the group consisting of surfactants, fabric softeners, softener precursor ester amines, softener precursor amido amines, hair conditioners, skin conditions, saccharides and polymers. In a second aspect it relates to a method of preparing such precusors. Further the invention relates to compositions, comprising the precursor of the invention.
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(2008/06/13)

Enantioselective hydrogenation of olefins with iridium-phosphanodihydrooxazole catalysts
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Lightfoot, Andrew,Schnider, Patrick,Pfaltz, Andreas
p. 2897 - 2899
(2007/10/03)

A Study of Enantioselective Reduction of para-Substituted 2-Methyl-cinnamaldehydes by Baker's Yeast
Reduction of a series of para-substituted 2-methyl-cinnamaldehydes (1-7) at 20°C and at pH = 2-3 afforded S-enantiomers of saturated alcohols 8-14 in 20-80% yield and 75 - ≥ 99% enantiomeric excess (e.e.); at 30°C, lower yields and e.e.s were obtained. Relative rates of the formation of allylic alcohols 15-21, catalyzed by alcohol dehydrogenase (ADH), correlate with the Hammett σ+ values of para-substituents, revealing that a more efficient delocalization of the positive charge on carbonylic carbon slow down the reduction rates, whereas no correlation of the electronic properties of the substituents with the rate of C=C double bond reduction, catalyzed by enoate reductase, is observed. On reduction of 3 by dried yeast in 2H2O, α,β-carbon atoms in 10a bear 2H atoms, in accordance with the previously reported hydrogenation of selectively 2H-labeled cinnamic aldehyde and cinnamic alcohol. The accumulated data indicate that the mechanism of the enone C=C bond reduction that comprises nucleophilic attack of the hydride ion species on the β-carbon in the first step, followed by enantioselective protonation on the α-carbon atom.
Sunjic, Vitomir,Majeric, Maja,Hamersak, Zdenko
p. 643 - 660
(2007/10/03)

Synthesis and Properties of the Enantiomers of the Two Artificial Fragrances Lilial and Methylundecanal
The enantiomers of the two artificial fragrances 3-(4-tert-butylphenyl)-2-methylpropanal (lilial) and 2-methylundecanal are synthesized with high enantiomeric purity using the SAMP/RAMP hydrazone method.The enantiomeric excesses are determined by HPLC via the corresponding SASP hydrazones.The olfactorial qualities of the enantiomers are described.
Enders, Dieter,Dyker, Hubert
p. 1107 - 1110
(2007/10/02)

Process for the manufacture of benzene derivatives
A novel process for the manufacture of p-tert.butylbenzene derivatives is described. The process comprises reacting p-tert.butyl-benzyl chloride with a 2-formylpropionate of the formula STR1 wherein R represents lower-alkyl, e.g. C1-6 -alkyl, especially methyl or ethyl, and, if desired, converting the resulting compound of the formula STR2 wherein R has the above significance, optionally after purification, into p-tert.butyl-α-methyl-hydrocinnamaldehyde by decarbalkoxylation.
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(2008/06/13)

Process for the preparation of p-t-butyl-α-methyldihydrocinnamaldehyde
This invention discloses a novel process for producing p-t-butyl-α-methyldihydrocinnamaldehyde which comprises converting the α-methyldihydrocinnamaldehyde to an enamine, oxazolidine or a Schiff's base, reacting said derivative with a tertiary butyl cation, and then removing the protective group.
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(2008/06/13)

HYDROGENATION OF CYCLAMEN ALDEHYDE AND LILY ALDEHYDE PRECURSORS ON SUPPORTED METAL CATALYSTS.
Cyclamen and lily aldehydes, which are widely used in the perfumery and cosmetics industry, are obtained by selective saturation of the double bond in 3-(4-isopropylphenyl)-2-methyl-2-propenal (cyclamen aldehyde precursor) and 3-(tert-butylphenyl)-2-methyl-2-propenal (lily aldehyde precursor). This paper reports the results of hydrogenation of cyclamen and lily aldehide precursors on supported catalysts in which the active phase was rhodium or nickel. Hydrogenation of cyclamen aldehyde precursor to cyclamen aldehyde on 5% Rh/Al//2O//3 or 30% Ni/SiO//2 proceeds with 95-99% selectivity; the selectivity of hydrogenation of lily aldehyde precursor is lower, owing to the specific characteristics of its structure.
Pak,Konuspaev,Sagindykov,Sokol'skii,Zapletal,Prykhlik
p. 1058 - 1060
(2007/10/02)

Conversion of Alkyl Acetates to (Siloxymethylene)alkanes by Co2(CO)8-Catalyzed Reaction with a Hydrosilane and Carbon Monoxide
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Chatani, Naoto,Murai, Shinji,Sonoda, Noboru
p. 1370 - 1372
(2007/10/02)

Heterocyclics useful as fungicides and fungicidal compositions thereof
Heterocyclic compounds characterized by the formula STR1 wherein R1, R3, R4, R5, R6, X and z are as hereinafter set forth, prepared, inter alia, by reacting a compound characterized by the formula STR2 with an amine characterized by the formula STR3 wherein R1, R3, R4, R5, R6, X and Y are as hereinafter set forth, are described. The end products are useful as fungicidal agents.
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(2008/06/13)