62267-02-1

Basic information

• Product Name: methyl phenylacetate-α-d1
• Synonyms: methyl phenylacetate-α-d1
• CAS NO: 62267-02-1
• Molecular Weight: 151.169
• Mol File: 62267-02-1.mol

Chemical Properties

• CAS DataBase Reference: methyl phenylacetate-α-d1(CAS DataBase Reference)
• NIST Chemistry Reference: methyl phenylacetate-α-d1(62267-02-1)
• EPA Substance Registry System: methyl phenylacetate-α-d1(62267-02-1)

Safety Data

• Hazardous Substances Data: 62267-02-1(Hazardous Substances Data)

Upstream product

• 13049-41-7 1,1-dimethoxy-2-phenylethene 
• 1455-13-6 deuteromethanol 
• 36140-84-8 1-(3,5-dimethyl-1H-pyrazol-1-yl)-2-phenylethan-1-one 
• 103-80-0 phenylacetyl chloride 
• 101-41-7 benzeneacetic acid methyl ester 

Relevant articles and documents

Nitrone/Imine Selectivity Switch in Base-Catalysed Reaction of Aryl Acetic Acid Esters with Nitrosoarenes: Joint Experimental and Computational Study

Herein we report a mild and diastereoselective access to ketonitrones by reacting easily available aryl acetic acid esters and other active methylene compounds, with nitrosoarenes under catalytic loading of 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP) at room temperature. Depending on the substitution pattern and nature of the aryl moiety, a switch toward the formation of imines can be observed. The mechanistic framework is put to scrutiny by experimental and theoretical studies, pointing to the formation of a nitroso aldol intermediate, whose fate toward one of the competing pathways, namely hydride transfer or elimination, would depend upon the NOH/CHα relative acidities. (Figure presented.).

Resolution of secondary alcohols using 2-acyl-3-phenyl-l-menthopyrazoles as enantioselective acylating agents

The chelation of AlCl3 with N-acylpyrazoles leads to structural fixation of the acyl moiety and an acceleration in the rate of acylation of secondary alcohols. The chiral environment of the fixed acyl moiety of 2-acyl-3-phenyl-l-menthopyrazole 2 causes diastereofacial selectivity in the reaction with secondary alcohols, and thus 2 behaves as an enantioselective acylating agent. By the use of 2.4 molar equivalents of racemic 1-phenylethanol 3a, 2-acetyl-3-phenyl-l-menthopyrazole 2a afforded (S)-1-phenylethyl acetate (S)-4aa enantioselectively and unreacted 3a was recovered with (R)-configuration. Furthermore, the inverse configurational preferences were observed to give (R)-4aa and (S)-3a by the addition of strongly basic amines, which sometimes behaved as catalysts for enolate formation from 2 and AlCl3. These dramatic changes in stereoselective preference should be useful properties of 2-acyl-3-phenyl-l-menthopyrazole 2 as an enantioselective acylating agent.

Mechanism of Acid-Catalyzed Hydrolysis of Phenylketene O,O and O,S Acetals

The hydrolysis of a phenylketene O,O acetal (1,1-dimethoxy-2-phenylethene, 1) and an O,S acetal have been studied kinetically at 30 deg C.The observed catalysis by general acids, the deuterium solvent isotope effects (kH2O/kD2O = 5.5 with 1), and the lack of nucleophilic acceleration by added 2-mercaptoethanol are in accord with a mechanism involving rate-determining protonation of the double bond.The nonlinear dependence of rate on formate buffer concentration was observed in the hydrolysis of 2, but it does not seem to be ascribable to a possible change in the rate-determining step in contrast to the previous suggestion.