Tert-Butylbenzene → 2-(1-Methylethoxy)-2-oxoethyl 2-hydroxy-2-phenylpropionate

HRID 1491547Notes

Reaction equation

HRID 1491547 reaction equation
[OH:1][C:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:9])[C:3](OCCCl)=[O:4].[C:16]([O:20][CH:21]([CH3:23])[CH3:22])(=[O:19])[CH2:17][OH:18].C(C1C=CC=CC=1)(C)(C)C>C(OCC)C>[OH:1][C:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:9])[C:3]([O:18][CH2:17][C:16]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])=[O:4]

Participants

5

Reactant 3

HCID 7366Tert-ButylbenzeneHCID 69338Isopropyl hydroxyacetateHCID 189532312-Chloroethyl 2-hydroxy-2-phenylpropionate2×

Product 1

HCID 544625652-(1-Methylethoxy)-2-oxoethyl 2-hydroxy-2-phenylpropionate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 4.5 mL aliquot of an ethyl ether solution containing 0.25M 2-chloroethyl 2-hydroxy-2-phenylpropionate, 0.25M isopropyl glycolate, and 1.0% tert-butylbenzene was added to 0.30 g Lipase P30. After mixing for 8 d at room temperature, the conversion of 2-chloroethyl 2-hydroxy-2-phenylpropionate to the title compound was estimated (by GC, Method B) to be approximately 10%. The GC peak assigned to the title compound was confirmed by HRMS calcd for C13H14O5Tms (M-CH3) 323.1314, obsd 323.1366.

Workup

  1. additionwas added to 0.30 g Lipase P30
  2. additionAfter mixing for 8 d at room temperature

Sources & evidence

ORD record
ord-bd059f05285442ebad861f2bc3cf2004
Source dataset
uspto-grants-1994_12
Patent number
US05371001

Reaction notes

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