261955-90-2

Basic information

• Product Name: Benzenemethanol, 4-ethoxy-alpha-methyl-, acetate, (-)- (9CI)
• Synonyms: Benzenemethanol, 4-ethoxy-alpha-methyl-, acetate, (-)- (9CI)
• CAS NO: 261955-90-2
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.25364
• Product Categories: ETHOXY
• Mol File: 261955-90-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzenemethanol, 4-ethoxy-alpha-methyl-, acetate, (-)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, 4-ethoxy-alpha-methyl-, acetate, (-)- (9CI)(261955-90-2)
• EPA Substance Registry System: Benzenemethanol, 4-ethoxy-alpha-methyl-, acetate, (-)- (9CI)(261955-90-2)

Safety Data

• Hazardous Substances Data: 261955-90-2(Hazardous Substances Data)

Upstream product

• 116071-56-8 1-(4-ethoxyphenyl)ethyl alcohol 
• 108-24-7 acetic anhydride 
• 1676-63-7 4'-ethoxyacetophenone 

Downstream Products

• 1260074-16-5 (S)-(-)-1-(4-ethoxyphenyl)ethyl acetate 
• 225920-04-7 (R)-(+)-1-(4-ethoxyphenyl) ethanol 

Relevant articles and documents

CAL-B-Catalyzed Enantioselective Deacetylation of Some Benzylic Acetate Derivatives Via Alcoholysis in Non-aqueous Media

Enantioselective deacetylation of a set of benzylic acetates via alcoholysis catalyzed by Lipase B from Candida antarctica (CAL-B), under mild conditions is described. A systematic study allows to determine the appropriate combination nucleophile/organic solvent and also to explain the influence of these parameters on the enzymatic catalytic reaction. In all cases, (R)-alcohols are obtained with high ee (up to >99 %) at conversion 36 % 500. The enzymatic reactivity is influenced by the hydrophobicity of solvent and the structure/nature of the nucleophile. Furthermore, CAL-B allows enantio-complementary between transesterifications in non-aqueous media: alcoholysis and acetylation.

A green route to enantioenriched (S)-arylalkyl carbinols by deracemization via combined lipase alkaline-hydrolysis/Mitsunobu esterification

Herein we report results of the chemoenzymatic deracemization of a range of secondary benzylic acetates 1a-9a via a sequence of hydrolysis with CAL-B lipase in non-conventional media, combined with esterification of the recovered alcohol according to the Mitsunobu protocol following an enzymatic kinetic resolution (KR). The KR of racemic acetates 1a-9a via an enzymatic hydrolysis, with CAL-B lipase and Na2CO3, in non-aqueous media was optimized and gave high selectivities (E ? 200) at good conversions (C >49%) for all of the substrates studied. This method competes well with the traditional one performed in a phosphate buffer solution. The deracemization using Mitsunobu inversion gave the (S)-acetates in moderate to excellent enantiomeric excess 75% ee 99%, in acceptable isolated yields 70% yield 89%, and with some variations according to the acetate structure.

Green methodology for enzymatic hydrolysis of acetates in non-aqueous media via carbonate salts

Herein we report a new approach to enantiomerically enriched acetates using a lipase-catalyzed hydrolysis in non-aqueous media by alkaline carbonate salts. The use of sodium carbonate in the enzymatic hydrolysis with Candida antarctica lipase B (CAL-B) of racemic acetates shows a large enhancement of the reactivity and selectivity of this lipase. The role of the carbonate salts, the amount and the nature of the alkaline earth metal on the efficiency of this new pathway are investigated. The enzymatic kinetic resolution of acetates 1a-9a, by enzymatic-carbonate hydrolysis under mild conditions is described. In all cases, the resulting alcohols and remaining acetates were obtained in high ee values (up to >99%) while the selectivities reached E >500.