- Synthesis method of p-hydroxyphenethyl alcohol
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The invention discloses a method for synthesizing p-hydroxyphenethyl alcohol from phenethyl alcohol as a raw material. The method comprises the steps as follows: firstly, phenethyl alcohol and acid anhydride are subjected to an esterification reaction to obtain phenethyl alcohol ester; then, phenethyl alcohol ester and acid anhydride are subjected to an electrophilic substitution reaction under the action of a catalyst and a catalyst promoter to obtain 4-acryl phenethyl alcohol ester; next, 4-acryl phenethyl alcohol ester and hydrogen peroxide are subjected to a Baeyer-Villiger oxidation reaction under the action of organic acid and an oxidation catalyst to obtain 4-acyloxy phenethyl alcohol ester; finally, the 4-acyloxy phenethyl alcohol ester is subjected to a hydrolysis reaction in alkaline water to obtain p-hydroxyphenethyl alcohol. The process for synthesizing p-hydroxyphenethyl alcohol has the advantages that raw materials are widely sourced, the yield is high, the process is concise, few three wastes are produced and industrialization is easy to realize.
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Paragraph 0038; 0046-0048
(2019/09/17)
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- Isopropenyl acetate: A cheap and general acylating agent of alcohols under metal-free conditions
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Functionalized primary, secondary and tertiary alcohols are efficiently acetylated by isopropenyl acetate and catalytic p-TsOH.
- Temperini, Andrea,Minuti, Lucio,Morini, Tommaso,Rosati, Ornelio,Piazzolla, Francesca
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p. 4051 - 4053
(2017/09/27)
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- TiCl4/Et3N-Mediated Condensation of Acetate and Formate Esters: Direct Access to β-Alkoxy- and β-Aryloxyacrylates
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A methodology to build (E)-β-alkoxy- and (E)-β-aryloxyacrylate moieties from acetate and formate esters promoted by the TiCl4/Et3N system is presented. The reaction is compatible with a broad range of structural skeletons and elapses through an unusual condensation pathway. Taking into account the obtained results, we propose a plausible mechanism involving a bimetallic titanium intermediate for this type of transformation.
- álvarez-Calero, José María,Jorge, Zacarías D.,Massanet, Guillermo M.
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supporting information
p. 6344 - 6347
(2016/12/23)
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- Solventless acetylation of alcohols and phenols catalyzed by supported iron oxide nanoparticles
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Supported iron oxide nanoparticles on silicate catalysts were found to be efficient and easily recoverable materials in the acetylation of alcohols and phenols to their corresponding acetyl compounds using acetic anhydride under mild and solvent-less conditions. The supported iron oxide nanoparticles could be easily recovered from the reaction mixture and reused ten times without any loss in activity.
- Rajabi, Fatemeh,Luque, Rafael
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p. 129 - 132
(2014/01/06)
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- Facile esterification of alcohols with 2-Acyl-4,5-dichloropyridazin-3(2 H)-ones under Friedel-Crafts conditions
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This paper describes the esterification of aromatic and aliphatic alcohols by using 2-acyl-4,5-dichloropyridazin-3(2H)-ones as an acyl source under Friedel-Crafts conditions. Twelve alcohols were reacted with four 2-acyl-4,5-dichloropyridazin-3(2H)-ones in the presence of AlCl3 in tetrahydrofuran at room temperature to give the corresponding esters in moderate to excellent yields. Thus, 2-acylpyridazin-3(2H)-ones serve as good and atom-economic acyl sources for the esterification of aromatic alcohols under Friedel-Crafts conditions, representing a rapid, practical, and efficient method of esterification. Georg Thieme Verlag Stuttgart. New York.
- Kim, Bo Ram,Sung, Gi Hyeon,Ryu, Ki Eun,Yoon, Hyo Jae,Lee, Sang-Gyeong,Yoon, Yong-Jin
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p. 1909 - 1915
(2014/08/18)
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- Selective acylation of the phenolic hydroxyl of (hydroxyalkyl)phenols by using vinyl carboxylates as acyl donors in the presence of rubidium fluoride
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Highly selective acylation of the phenolic hydroxy group can be achieved with (hydroxyalkyl)phenols carrying both alcoholic and phenolic hydroxyls by the use of vinyl carboxylates as acyl donors in the presence of rubidium fluoride.
- Miyazawa, Toshifumi,Yamamoto, Masato,Danjo, Hiroshi
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p. 1351 - 1354
(2013/10/01)
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- A new ferrocene-based bulky pyridine as an efficient reusable homogeneous catalyst
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An effective approach to reusing a homogeneous catalyst has been demonstrated. A ferrocene-based bulky pyridine has been synthesized and utilized as a homogeneous catalyst for the synthesis of benzoylfumarates as well as for acetylation. After the reaction, the catalyst was separated by simple precipitation and reused without appreciable loss of activity. The Royal Society of Chemistry 2013.
- Kashyap, Bishwapran,Phukan, Prodeep
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p. 15327 - 15336
(2013/09/02)
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- Microwave-accelerated selective acylation of (hydroxyalkyl)phenols using acid chlorides
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Highly selective acylation of the alcoholic hydroxy group can be achieved with (hydroxyalkyl)phenols carrying both alcoholic and phenolic hydroxyls by the use of the most common acylating agents, acid chlorides, under microwave irradiation. Copyright Tayl
- Miyazawa, Toshifumi,Yamamoto, Masato,Maeda, Yuki
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experimental part
p. 1092 - 1099
(2009/09/06)
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- COMPOUNDS
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The present invention provides the use of a compound of the Formula: (I) wherein R1 is C1-5 alkoxy, OCOC1-3Alkyl, O(CH2)2O(CH2)2O(CH2)2OMe, O(CH2)2O(CH2)2O(CH2)2OH or OH; R2 is H, (CH2)nOH, OCH3, Hal or (II) or (III) R3 is H or (CH2)nOH; and R4 is C1-6 alkyl, optionally substituted by one or more of Hal, OH, COCH3, NH2, NHCH3, NHMe, NMe2, OCOCH3, CO2H or esters or amides thereof where n is 1-5; and pharmaceutically acceptable salts thereof, in the manufacture of a medicament for use in modulating PKB activity.
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Page/Page column 14-15
(2009/09/08)
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- Biological activity of acetylated phenolic compounds
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In recent years an effort has been made to isolate and identify biologically active compounds that are included in the Mediterranean diet. The existence of naturally occurring acetylated phenolics, as well as studies with synthetic ones, provide evidence that acetyl groups could be correlated with their biological activity. Platelet activating factor (PAF) is implicated in atherosclerosis, whereas its inhibitors seem to play a protective role against cardiovascular disease. The aim of this study was to examine the biological activity of resveratrol and tyrosol and their acetylated derivatives as inhibitors of PAF-induced washed rabbit platelet aggregation. Acetylation of resveratrol and tyrosol was performed, and separation was achieved by HPLC. Acetylated derivatives were identified by negative mass spectrometry. The data showed that tyrosol and its monoacetylated derivatives act as PAF inhibitors, whereas diacetylated derivatives induce platelet aggregation. Resveratrol and its mono- and triacetylated derivatives exert similar inhibitory activity, whereas the diacetylated ones are more potent inhibitors. In conclusion, acetylated phenolics exert the same or even higher antithrombotic activity compared to the biological activity of the initial one.
- Fragopoulou, Elizabeth,Nomikos, Tzortzis,Karantonis, Haralabos C.,Apostolakis, Constantinos,Pliakis, Emmanuel,Samiotaki, Martina,Panayotou, George,Antonopoulou, Smaragdi
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- Optimization of lipase-catalyzed synthesis of acetylated tyrosol by response surface methodology
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The ability of a noncommercial immobilized lipase from Staphylococcus xylosus (SXLi) to catalyze the transesterification of tyrosol and ethyl acetate was investigated. Response surface methodology was used to evaluate the effects of the tempera
- Aissa, Imen,Bouaziz, Mohamed,Ghamgui, Hanen,Kamoun, Amel,Miled, Nabil,Sayadi, Sami,Gargouri, Youssef
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experimental part
p. 10298 - 10305
(2009/09/25)
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- Highly efficient and versatile acetylation of alcohols catalyzed by cerium(III) triflate
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Cerium(III) triflate is a powerful catalyst for the acetylation of alcohols. The reaction works well for a large variety of simple and functionalized alcohols, without isomerisation of chiral centres. Changes of hydroxyl protective groups are possible in a one-pot procedure. The catalyst can be easily recycled.
- Dalpozzo, Renato,De Nino, Antonio,Maiuolo, Loredana,Procopio, Antonio,Nardi, Monica,Bartoli, Giuseppe,Romeo, Roberto
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p. 5621 - 5624
(2007/10/03)
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- Determination of phenols, flavones, and lignans in virgin olive oils by solid-phase extraction and high-performance liquid chromatography with diode array ultraviolet detection
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A simple analytical method for the quantitative determination of phenols, flavones, and lignans in virgin olive oils was developed. The polar fraction was isolated from small amounts of oil sample (2.5 g) by solid-phase extraction (SPE) using diol-phase cartridges, and the extract was analyzed by reversed-phase HPLC coupled with diode array LTV detection. Chromatographic separation of pinoresinol, cinnamic acid, and 1-acetoxypinoresinol was achieved. Repeatability (RSD 90%), and response factors for each identified component were determined. SPE on amino-phase cartridges was used for isolating acidic phenols and as an aid for phenol identification. For the first time, 2-(4-hydroxyphenyl)ethyl acetate was detected in olive oils. The aldehydic structure of the ligstroside aglycon was confirmed by NMR spectroscopy. The colorimetric determination of total o-diphenolic compounds by reaction with molybdate was consistent with their HPLC determination. Differences between results obtained by liquid-liquid extraction and SPE were not statistically significant.
- Mateos, Raquel,Espartero, Jose Luis,Trujillo, Mariana,Rios,Leon-Camacho, Manuel,Alcudia, Felipe,Cert, Arturo
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p. 2185 - 2192
(2007/10/03)
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- Mild and practical acylation of alcohols with esters or acetic anhydride under distannoxane catalysis
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Distannoxane catalysts effect acylation of alcohols by action of esters and acetic anhydride. In particular, use of enol esters provides an extremely useful method. Primary alcohols are acylated in preference to secondary ones as well as phenol. Both acid- and base-sensitive functional groups remain intact. Especially unique is the discrimination of thio function which is completely tolerant under the present reaction conditions. This method is highly practical since operation is quite simple. Esters and solvents can be used without purification and no inert atmosphere is necessary. The products can be isolated simply by column chromatography or distillation without aqueous workup.
- Orita, Akihiro,Sakamoto, Katsumasa,Hamada, Yuji,Mitsutome, Akihiro,Otera, Junzo
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p. 2899 - 2910
(2007/10/03)
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- An Extremely Powerful Acylation Reaction of Alcohols with Acid Anhydrides Catalyzed by Trimethylsilyl Trifluoromethanesulfonate
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Trimethylsilyl trifluoromethanesulfonate is an excellent catalyst for the acylation of alcohols with acid anhydrides. Highly functionalized primary, secondary, tertiary, and allylic alcohols, and phenols, were acylated cleanly and efficiently and in a fraction of the time used under the standard DMAP conditions.
- Procopiou, Panayiotis A.,Baugh, Simon P.D.,Flack, Stephen S.,Inglis, Graham G.A.
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p. 2342 - 2347
(2007/10/03)
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- Biogeneration and Biodegradation of Raspberry Ketone in the Fungus Beauveria bassiana
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In growing cultures of the fungus Beauveria bassiana (ATCC 7159) the incubation of 4-(4′-hydroxyphenyl)but-3-en-2-one (p-hydroxybenzylidenacetone, 3), of 4-(4′-hydroxyphenyl)butan-2-one (raspberry ketone, 1), and of the S and R,S forms of 4-(4′-hydroxyphenyl)butan-2-ol (2) yields 2-(4′-hydroxyphenyl)ethanol (tyrosol, 4) as a final product. The experiments support the view that the actual substrate for the Baeyer-Villiger-type degradation is raspberry ketone (1) and that there is a kinetic preference in the microbial enzymatic system for the oxidation to 1 of the S form of the 4-(4′-hydroxyphenyl)butan-2-ol (2).
- Fuganti, Claudio,Mendozza, Monica,Joulain, Daniel,Minut, Jose,Pedrocchi-Fantoni, Giuseppe,Piergianni, Valentino,Servi, Stefano,Zucchi, Gioia
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p. 3616 - 3619
(2007/10/03)
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- Regio- and Chemo-selective Properties of Lipase from Candida cylindracea
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Lipase from Candida cylindracea allows discrimination between the two connectively non-equivalent hydroxy groups in primary diols or their esters via acylation-hydrolysis, with high regioselectivity.The same technique is used to distinguish between hydroxy groups of different nature in phenolic compounds.
- Pedrocchi-Fantoni, Giuseppe,Servi, Stefano
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p. 1029 - 1034
(2007/10/02)
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- SELECTIVE ACYLATIONS OF AMINOPHENOLS AND HYDROXYALKYLPHENOLS WITH 1-ACETYL-v-TRIAZOLOPYRIDINE.
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The title triazolide serves as a convenient reagent for highly chemoselective acetylations of aminophenols and hydroxyalkylphenols.
- Paradisi, Mario Paglialunga,Zecchini, Giampiero Pagani,Torrini, Ines
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p. 5029 - 5032
(2007/10/02)
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- 3-ACYL-2-OXAZOLONE-ZIRCONIUM COMPLEXES AS EXCELLENT REAGENTS FOR HIGHLY REGIOSELECTIVE ACYLATION OF POLYALCOHOLS
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In combination with 3-acyl-2-oxazolones, zirconium complexes such as zirconium acetylacetonate and zirconocene chloride hydride-Mg serve well as effective catalysts for regioselective acylation of polyalcohols including 1,2-diols to permit higly preferential protection of primary hydroxyl groups.
- Kunieda, Takehisa,Mori, Takashi,Higuchi, Tsunehiko,Hirobe, Masaaki
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p. 1977 - 1980
(2007/10/02)
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- HIGHLY SELECTIVE ACYLATION OF AMINES AND ALCOHOLS BY POLY(3-ACYL-2-OXAZOLONE)
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Poly(3-acyl-2-oxazolone) serves as a convenient reagent for highly chemo- and regioselective acylation of polyamines, amino-alcohols and polyalcohols.
- Kunieda, Takehisa,Higuchi, Tsunehiko,Abe, Yoshihiro,Hirobe, Masaaki
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p. 1159 - 1160
(2007/10/02)
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