- A 4 - isobutyl phenyl ketone compounds (by machine translation)
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The invention discloses a 4 - isobutyl phenyl ketone compounds, the compound structure is as follows: said compound 4 - isobutyl-benzene as the starting material, substituted sulfonic acid and substituted sulfonate as the catalyst, the reaction with the acyl chloride, the following reaction: the application of this method to synthesize 4 - isobutyl phenyl ketone compound, simple and convenient operation, mild reaction conditions, environment-friendly, and has excellent industrial prospect. (by machine translation)
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Paragraph 0037; 0038
(2017/08/25)
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- Synthesis method of silver aldehyde spice
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The invention discloses a synthesis method of a silver aldehyde spice and relates to the technical field of fine chemical engineering. Isobutyl benzene and propionyl chloride are used as starting raw materials, silver aldehyde is synthesized through acylation reaction and hydrodechlorination, the raw materials in use are easy to obtain, and the product yield is high. Ethyl alcohol serves as an organic solvent for hydrogenation reaction, the shortcomings of incomplete reaction or excessive hydrogenation and inactivation after mechanical application of a catalyst in the hydrogenation process are overcome, the content of meta-position silver aldehyde and ortho-position silver aldehyde during side reaction is controlled to be 0.5% or below, the content of 2-methyl-3(4-(2-methyl propyl) phenyl) propyl alcohol in a silver aldehyde finished product is controlled to be 0.5% or below, the unimodal content of the silver aldehyde product can be 98.5% or above, and the silver aldehyde spice has a pure and soft aroma and meets the flavoring requirements of essences and spices.
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Paragraph 0049-0055; 0074-0080
(2017/02/24)
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- Synthesis method of p-isobutyl-beta-chloro-alpha-methyl allyl benzene aldehyde
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The invention discloses a synthesis method of p-isobutyl-beta-chloro-alpha-methyl allyl benzene aldehyde and relates to the technical field of fine chemical engineering. The synthesis method includes: using isobutylbenzene and propionyl chloride as raw materials, and generating p-isobutyl propiophenone through acylation reaction; enabling p-isobutyl propiophenone to be in acylation reaction with phosphorus oxychloride to obtain a silver aldehyde precursor- p-isobutyl-beta-chloro-alpha-methyl allyl benzene aldehyde. The synthesis method is easy-to-get in raw materials, high in yield and convenient for industrial large-scale production; content of byproducts-ortho- and meta-isobutyl-beta-chloro-alpha-methyl allyl benzene aldehyde is controlled below 0.2%, and impurity content in a final silver aldehyde product prepared after hydrodechlorination is controlled effectively, so that flavoring requirements of essence and flavor are met.
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Paragraph 0039; 0040-0046; 0054-0061
(2017/10/20)
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- Stereoselective Ketone Rearrangements with Hypervalent Iodine Reagents
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The first stereoselective version of an iodine(III)-mediated rearrangement of arylketones in the presence of orthoesters is described. The reaction products, α-arylated esters, are very useful intermediates in the synthesis of bioactive compounds such as ibuprofen. With chiral lactic acid-based iodine(III) reagents product selectivities of up to 73 % ee have been achieved.
- Malmedy, Florence,Wirth, Thomas
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supporting information
p. 16072 - 16077
(2016/10/30)
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- The digital code driven autonomous synthesis of ibuprofen automated in a 3D-printer-based robot
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An automated synthesis robot was constructed by modifying an open source 3D printing platform. The resulting automated system was used to 3D print reaction vessels (reactionware) of differing internal volumes using polypropylene feedstock via a fused deposition modeling 3D printing approach and subsequently make use of these fabricated vessels to synthesize the nonsteroidal antiinflammatory drug ibuprofen via a consecutive one-pot three-step approach. The synthesis of ibuprofen could be achieved on different scales simply by adjusting the parameters in the robot control software. The software for controlling the synthesis robot was written in the python programming language and hard-coded for the synthesis of ibuprofen by the method described, opening possibilities for the sharing of validated synthetic 'programs' which can run on similar low cost, user-constructed robotic platforms towards an 'open-source' regime in the area of chemical synthesis.
- Kitson, Philip J.,Glatzel, Stefan,Cronin, Leroy
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supporting information
p. 2776 - 2783
(2017/01/09)
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- A three-minute synthesis and purification of ibuprofen: Pushing the limits of continuous-flow processing
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In a total residence time of three minutes, ibuprofen was assembled from its elementary building blocks with an average yield of above 90% for each step. A scale-up of this five-stage process (3 bond-forming steps, one work-up, and one in-line liquid-liquid separation) provided ibuprofen at a rate of 8.09 gh-1 (equivalent to 70.8 kg y-1) using a system with an overall footprint of half the size of a standard laboratory fume hood. Aside from the high throughput, several other aspects of this synthesis expand the capabilities of continuous-flow processing, including a Friedel-Crafts acylation run under neat conditions and promoted by AlCl3, an exothermic in-line quench of high concentrations of precipitation-prone AlCl3, liquid-liquid separations run at or above 200 psi to provide solvent-free product, and the use of highly aggressive oxidants, such as iodine monochloride. The use of simple, inexpensive, and readily available reagents thus affords a practical synthesis of this important generic pharmaceutical.
- Snead, David R.,Jamison, Timothy F.
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supporting information
p. 983 - 987
(2015/03/05)
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- DMF Dimethyl Acetal as Carbon Source for α-Methylation of Ketones: A Hydrogenation-Hydrogenolysis Strategy of Enaminones
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A novel heterogeneous catalytic hydrogenation-hydrogenolysis strategy has been developed for the α-methylation of ketones via enaminones using DMF dimethyl acetal as carbon source. This strategy provides a very convenient route to α-methylated ketones using a variety of ketones without any base or oxidant. (Chemical Equation Presented).
- Borah, Ashwini,Goswami, Limi,Neog, Kashmiri,Gogoi, Pranjal
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p. 4722 - 4728
(2015/05/13)
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- The continuous-flow synthesis of ibuprofen
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Let relief flow forth I A three-step, continuous-flow synthesis of ibuprofen was accomplished using a simplified microreactor. By designing a synthesis in which excess reagents and byproducts are compatible with downstream reactions, no intermediate purification or isolation steps are required.
- Bogdan, Andrew R.,Poe, Sarah L.,Kubis, Daniel C.,Broadwater, Steven J.,McQuade, D. Tyler
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supporting information; experimental part
p. 8547 - 8550
(2009/12/31)
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- 5-Aryl-imidazolin-2-ones as a scaffold for potent antioxidant and memory-improving activity
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A series of 5-phenyl-substituted-N-alkyl-imidazolin-2-ones with potent radical-scavenging activity and lipid peroxidation inhibitory activity was synthesized. Many of the compounds showed memory-improving effect in animal models independent of the inhibitory activity on lipid peroxidation.
- Watanabe, Kazutoshi,Morinaka, Yasuhiro,Hayashi, Yoshio,Shinoda, Masaki,Nishi, Hiroyoshi,Fukushima, Nobuko,Watanabe, Toshiaki,Ishibashi, Akira,Yuki, Satoshi,Tanaka, Masahiko
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p. 1478 - 1483
(2008/09/18)
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- 4-(Benzoylindolizinyl)butyric acids; novel nonsteroidal inhibitors of steroid 5α-reductase. III
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A novel series of indolizinebutyric acids with various benzoyl substituents was synthesized to develop nonsteroidal inhibitors of steroid 5α-reductase, and the structure-activity relationships in this series were studied. We previously reported the structure-activity relationships in a series of indolebutyric acids as well as the discovery of the novel nonsteroidal 5α-reductase inhibitor, FK143. We have now made other modifications to this compound to improve in vivo inhibitory activity. By altering the heterocyclic nucleus and changing the benzoyl substituent we have succeeded in identifying the strongly active compound, FK687, (S)-4-[1-[4-[[1-(4-isobutylphenyl)butyl]oxy]benzoyl]indolizin-3-yllbutyric acid, which displays strong in vitro inhibitory activity against the human enzyme and in vivo inhibitory activity against the castrated young rat model. This compound should be a useful agent for the treatment of benign prostatic hyperplasia.
- Sawada,Okada,Kuroda,Watanabe,Sawada,Tanaka
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p. 799 - 813
(2007/10/03)
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- Photochemical Rearrangement of α-Chloro-Propiophenones to α-Arylpropanoic Acids: Studies on Chirality Transfer and Synthesis of (S)-(+)-Ibuprofen and (S)-(+)-Ketoprofen
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A new single-step efficient photochemical approach for α-arylpropanoic acids (4) from α-chloro-propiophenones (5) is described.It involves carbonyl triplet excited state directed 1,2-aryl migration of the aryl group which has been found to be highly dependent upon the nature of the aryl substituent.The mode of the rearrangement is probed by the study of the photobehaviour of a set of optically active α-chloro-propiophenones.The results suggest that the nature of the carbonyl triplets (n, ?*/ ?, ?*) plays an important role in the chirality transfer.This method finds application in the synthesis of optically active ibuprofen (4e) and ketoprofen (26), though in moderate optical yields.
- Sonawane, Harikisan,Bellur, Nanjundiah S.,Kulkarni, Dilip G.,Ayyangar, Nagaraj R.
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p. 1243 - 1260
(2007/10/02)
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- INDOLE DERIVATIVES AND THEIR USE FOR TESTOSTERONE 5-ALPHA-REDUCTASE-MEDIATED DISEASES
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Indole derivatives of the formula and pharmaceutical compositions thereof. They are useful for treating or preventing testosterone 5-alpha-reductase-mediated diseases, such as alopecia, acnes and prostatism
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- Intermediates for preparing optically active carboxylic acids
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A process is described for preparing optically active alpha-arylalkanoic acids consisting of rearranging an optically active ketal of formula STR1 in which the substituents have the meaning given in the description of the invention.
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- Oxidative Rearrangement of Aryl Ethyl Ketones to Alkyl 2-Arylpropanoates by Lead(IV) Acetate
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Treatment of the propiophenones p-R'C6H4COCH2Me (1; R' = H, Me, Bui, Ph, Br) with lead(IV) acetate in trialkyl orthoformate in the presence of acid catalyst is found to give alkyl esters of 2-arylpropanoic acids (2) in good to excellent yields via 1,2-aryl migration in (1).Hydrolysis of (2) leads to the corresponding acids, some of which are important pharmaceutical compounds.The rate of aryl migration increases when the substituent R' is an electron-releasing group such as methyl, isobutyl, or phenyl.The rate of rearrangement of the dimethyl acetals of (1); R' = H, Bui, Ph) is nearly the same as that of (1).Such rearrangement hardly occurs in the absence of acid catalyst.A reaction pathway involving the formation of a monoalkoxylead(IV) compound, and its decomposition accompanied with aryl migration is discussed.
- Yamauchi, Takayoshi,Nakao, Kenji,Fujii, Kyoichi
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p. 1433 - 1436
(2007/10/02)
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- Process for preparing α-hydroxy-alkanoic acids and compounds obtained by this process
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The invention relates to a process for preparing α-hydroxy-alkanoic acids of general formula: STR1 in which R represents hydrogen or a lower alkyl radical and Cy represents phenyl or a heterocyclic radical, both radicals optionally comprising one or more substituents selected from the group consisting of lower alkyl, lower alkenyl, lower alkynyl radicals and halogen atoms, process which comprises the treatment of an α,α-dihalogenated ketone of general formula: STR2 in which R and Cy have the same meaning as above and X represents chlorine, bromine or iodine, in the presence of an aqueous solution of an alkali metal hydroxide and a non polar organic solvent selected from an aromatic or alicyclic hydrocarbon, the treatment being carried out at a temperature between the boiling temperature of the reaction medium at atmospheric pressure and 240° C. under pressure and the alkali metal so formed is then acidified to obtain the desired acid.
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- Manufacture of alpha-arylalkanoic acids and precursors
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α-Arylalkanoic acids or esters, orthoesters or amides thereof are prepared by forming an α-hydroxy ketal or thioketal of an aryl alkyl ketone, activating the α-hydroxy substituent with an esterifying agent to form the corresponding ketal or thioketal ester substrate, wherein the ester group is sufficiently labile to non-catalytically disassociate from the substrate in a protic or dipolar, aprotic solvent, maintaining the ester substrate in contact with the protic or dipolar, aprotic solvent or mixtures thereof for a time sufficient to form the corresponding α-arylakanoic acid or ester, orthoester or amide thereof, and optionally concomitantly or sequentially hydrolyzing any ester, orthoester or amide formed to the corresponding α-arylalkanoic acid.
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- New methods and reagents in organic synthesis. 35. A new synthesis of some non-steroidal anti-inflammatory agents with the 2-arylpropionic acid skeleton by the use of diphenyl phosphorazidate (DPPA) as a 1,3-dipole
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Reaction of diphenylphosphonic azide (8) with the pyrrolidine enamine 13 of 4-isobutylpropiophenone afforded two amidines 15a and 16a, which were derived from the 1,3-dipolar cycloadduct 14a by the expulsion of nitrogen followed by 1,2-aryl migration (path a) and by 1,3-dipolar elimination (path b), respectively. Although diphenylthiophosphinic azide (9) and ethyl phenylthiophosphonoazidate (10) also gave similar results, diphenylphosphorazidate (DPPA, (C6H5O)2P(O)N3) furnished the amidine 15d formed via path a as the sole isolable product. Hydrolysis of 15d with potassium hydroxide afforded ibuprofen (3) in good yield. Other nonsteroidal antinflammatory agents, naproxene (4), ketoprofen (5), and flurbiprofen (6), were analogously and conveniently prepared from the ketones 17, 22, and 25, respectively, by a similar three-step operation using pyrrolidine, DPPA, and potassium hydroxide. 2-(2-Dibenzofuranyl)-propionic acid (7) was also prepared from the ketone 28 by the three-step procedure.
- Kawai,Kato,Hamada,Shioiri
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p. 3139 - 3148
(2007/10/02)
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- Process for oxidizing thallium (I) to thallium (III)
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Thallium (l) alkanoate salts are oxidized to thallium (lll) salts in a liquid medium with a peroganic carboxylic acid in the presence of a reactive form of manganese or ruthenium.
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- Process for preparing arylalkanoic acid derivatives
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2-Aryl-C3 to C6 -alkanoate esters are prepared economically by reacting an enol ether of an aryl alkyl ketone with a trivalent thallium salt in an organic solvent. The trivalent thallium ions can be regenerated by adding a peracid and a reactive form of manganese, ruthenium, cobalt, iridium, hafnium, osmium or neobium to oxidize monovalent thallium ions to the trivalent state, in a sequential, continuous or stoichiometric procedure. The ester intermediate product is then converted to the corresponding 2-aryl-C3 - to C6 -alkanoic acid or salt thereof. The aryl group is selected so the resulting acid product will be a useful compound such as anti-inflammatory, analgesic and anti-pyretic drug or agriculturally useful product. Examples of drug acids which can be made by this process include ibuprofen, flurbiprofen, fenoprofen and naproxen and the like.
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- Process for preparing arylalkanoic acid derivatives
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2-Aryl-C3 to C6 -alkanoate esters are prepared economically by reacting an enol ether of an aryl alkyl ketone with a trivalent thallium salt in an organic solvent. The trivalent thallium ions can be regenerated by adding a peracid and a reactive form of manganese, ruthenium, cobalt, iridium, hafnium, osmium or neobium to oxidize monovalent thallium ions to the trivalent state, in a sequential, continuous or stoichiometric procedure. A continuous process using a Scheibel column is disclosed. The ester intermediate product is then converted to the corresponding 2-aryl-C3 - to C6 -alkanoic acid or salt thereof. The aryl group is selected so the resulting acid product will be a useful compound such as an anti-inflammatory, analgesic and anti-pyretic drug or agriculturally useful product. Examples of drug acids which can be made by this process include ibuprofen, flurbiprofen, fenoprofen and naproxen and the like.
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