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

HRID 1491546Notes

Reaction equation

HRID 1491546 reaction equation
[OH:1][CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3](OCCCl)=[O:4].[C:15]([O:19][CH:20]([CH3:22])[CH3:21])(=[O:18])[CH2:16][OH:17].C(C1C=CC=CC=1)(C)(C)C>C(OCC)C>[OH:1][CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:17][CH2:16][C:15]([O:19][CH:20]([CH3:22])[CH3:21])=[O:18])=[O:4]

Participants

5

Reactant 3

HCID 7366Tert-ButylbenzeneHCID 69338Isopropyl hydroxyacetateHCID 252572Mandelic acid, 2-chloroethyl ester2×

Product 1

HCID 536777992-(1-Methylethoxy)-2-oxoethyl 2-hydroxy-2-phenylacetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 6 mL aliquot of an ethyl ether solution containing 0.25M 2-chloroethyl 2-hydroxy-2-phenylacetate, 0.25M isopropyl glycolate, and 1.0% tert-butylbenzene was added to 0.43 g Lipase P30. After mixing for 5 d at room temperature, the conversion of 2-chloroethyl 2-hydroxy-2-phenylacetate to the title compound was estimated (by GC, Method B) to be approximately 15%. The GC peak assigned to the title compound was confirmed by HRMS: calcd for C12H12O5Tms (M-CH3) 309.1158, obsd 309.1171. In identical reactions substituting Lipase G, Lipase AK, Lipase MAP10, Protease M, Lipase AP12, or porcine pancreatic lipase for Lipase P30, the relative values for conversions at 5 d (Lipase P30=100) were 17, 12, 12, 6, 4, and 2%, respectively.

Workup

  1. additionwas added to 0.43 g Lipase P30
  2. additionAfter mixing for 5 d at room temperature

Sources & evidence

ORD record
ord-544f5dc8bfbe4b769972c809863300a6
Source dataset
uspto-grants-1994_12
Patent number
US05371001

Reaction notes

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