10522-02-8

Upstream product

• 7064-06-4 3-methyl-5-phenyl-4,5-dihydroisoxazole 
• 5381-93-1 1-hydroxy-1-phenyl-3-butanone 
• 93-56-1 phenylethane 1,2-diol 
• 108-24-7 acetic anhydride 
• 61235-70-9 (+/-)4-phenyl-2,2-di-n-butyl-1,3,2-dioxa stannolan 
• 830-03-5 4-nitrophenol acetate 
• 1363906-80-2 1-acetyl-2,3,4,6,7,8-hexahydropyrrolo[1,2-a]pyrimidinium tetraphenylborate 
• 2466-76-4 N-Acetylimidazole 
• 70-11-1 α-bromoacetophenone 
• 2243-35-8 2-acetoxyacetophenone 
• 6270-03-7 1,2-diacetoxy-1-phenyl-ethane 
• 100-42-5 styrene 
• 25779-13-9 (S)-1-phenyl-1,2-ethanediol 
• 64-19-7 acetic acid 

Relevant academic research and scientific papers

Selective acylation of a sterically hindered hydroxyl group of unsymmetrical diols containing a primary hydroxyl group such as 1,5-hexanediol in the presence of silica gel with acetyl chloride

The selective acetylation of sterically hindered hydroxyl groups of 1,5-hexanediol preadsorbed on silica gel was reported. The relation between the adsorption of the diol on SiO2 and its reactivity for selective acetylation was studied. Results demonstrated that unsymmetrical diols get adsorbed on the surface of SiO2 preferentially via a primary OH group, leaving the non-adsorbed OH group available for reaction.

Preparation of the enantiomers of 1-phenylethan-1,2-diol. Regio- and enantioselectivity of acylase I and Candida antarctica lipases A and B

Acylase I and Candida antarctica lipases A (CAL-A) and B (CAL-B) were evaluated for the preparation of the enantiomers of 1-phenylethan-1,2-diol. In the presence of CAL-B, the sequential one-pot methanolysis of the diacetate in acetonitrile allowed the preparation of (S)-diol (e.e. 97%) and (R)-1-acetoxy-1-phenylethanol (e.e. 94%). Base-catalyzed methanolysis of the monoacetate resulted in the corresponding (R)-diol. When one of the diol enantiomers was subjected to Mitsunobu esterification, inversion of configuration occurred, allowing transformation of the initially racemic mixture to one enantiomer. Acylase I-catalysis led to the chemo- and enantioselective formation of (S)-1-acetoxy-1-phenylethanol (e.e. 97%) in the presence of the primary hydroxyl function through acetylation of the secondary hydroxyl group. The low chemical yield (ca. 25%) was due to the moderate enzymatic regioselectivity. CAL-A behaved in a similar way to acylase I.

TiCl3(OTf) and TiO(TFA)2 efficient catalysts for ring opening of epoxides with alcohols, acetic acid and water

TiCl3 (OTf) and TiO(TFA)2 can efficiently catalyze nucleophilic ring opening of epoxides in primary, secondary and tertiary alcohols, acetic acid and water to give the corresponding β-alkoxy alcohols, β-acetoxy alcohols and vicinal diols with high stereo- and regioselectivity in excellent yields. The reaction of optically active styrene oxide in MeOH with two titanium reagents was found to be highly stereospecific and afforded the corresponding S-(+)-2-methoxy-2-phenyl ethanol in 89-95% ee.

Investigation of the catalytic activity of an electron-deficient vanadium(IV) tetraphenylporphyrin: A new, highly efficient and reusable catalyst for ring-opening of epoxides

In this work, the catalytic activity of high-valent tetraphenylporphyrinatovanadium(IV) trifluoromethanesulfonate, [V IV(TPP)(OTf)2], in the nucleophilic ring-opening of epoxides is reported. This new V(IV) catalyst was used as an efficient catalyst for alcoholysis with primary (methanol, ethanol and n-propanol), secondary (iso-propanol) and tertiary alcohols (tert-butanol), hydrolysis and acetolysis of epoxides with acetic acid and also for the conversion of epoxides to 1,2-diacetates with acetic anhydride, conversion of epoxides to thiiranes with ammonium thiocyanate and thiourea, and for conversion of epoxides to acetonides with acetone. The catalyst was reused several times without loss of its activity.

Regioselective acetylation of carbohydrates and diols catalyzed by tetramethyl-ammonium hydroxide in water

A novel method for an efficient regioselective acetylation of carbohydrates and diols in aqueous solution is described. Treatment of substrates with 1-acetylimidazole, and tetramethyl-ammonium hydroxide (TMAH) in water under mild conditions gave highly regioselective acetylation for primary hydroxyl groups. This discovery provides an eco-friendly way for selective acetylation of non-protected glycosides and diols in water, avoiding the use of toxic organic solvents and the necessity of pre-protection of secondary hydroxyl groups. This journal is

OXIDATION OF ISOXAZOLINES BY PERACIDS - A USEFUL ROUTE TO β-HYDROXY KETONES AND ACYLATED DIOLS

A method for bringing about the ring cleavage of isoxazolines by the use of peracids is described.

A highly efficient protocol for regioselective ring-opening of epoxides with alcohols, water, acetic acid, and acetic anhydride catalyzed by SbF3

SbF3as an efficient catalyst has been used for regioselective alcoholysis, acetolysis and hydrolysis of epoxides to the corresponding β-alkoxy, β-acetoxy alcohols, and 1,2-diols in high to excellent yields. This study also represents a convenient synthesis of vic-diacetates from ring-opening of epoxides with acetic anhydride.

Synthesis and characterization of a novel Fe3O4@SiO2/bipyridinium dichloride nanocomposite and its application as a magnetic and recyclable phase-transfer catalyst in the preparation of β-azidoalcohols, β-cyanohydrins, and

β-Azidoalcohols, β-cyanohydrins, and β-acetoxy alcohols have been synthesized in the presence of a Fe3O4@SiO2/bipyridinium nanocomposite (Fe3O4@SiO2/BNC) as a novel magnetic and recyclable

Mild and efficient ring opening of epoxides catalyzed by potassium dodecatungstocobaltate(III)

Efficient ring opening of epoxides under mild conditions is reported. Potassium dodecatungstocobaltate(III) trihydrate was used as an efficient catalyst for the alcoholysis and acetolysis of epoxides. Conversion of epoxides to thiiranes was also performed efficiently in the presence of this catalyst. Springer-Verlag 2005.

Efficient and regioselective ring-opening of epoxides with carboxylic acid catalyzed by graphite oxide

An efficient, simple and regioselective ring-opening reaction of epoxides with various carboxylic acids under metal-free conditions is reported. The ring-opening of epoxides takes place in the presence of graphite oxide as an efficient and available catalyst to produce the corresponding 2-hydroxy monoester and 1,2-diester derivatives in good yields. Regioselective attack of the nucleo-phile, short reaction times, metal-free conditions and reusability of catalyst are among the advantages of the present protocol.