Tert-Butylbenzene → 2-(1-Methylethoxy)-2-oxoethyl 2-hydroxy-3-phenylpropionate

HRID 1491549Notes

Reaction equation

HRID 1491549 reaction equation
[OH:1][CH:2]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[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][CH:2]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[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 189532302-Chloroethyl 2-hydroxy-3-phenylpropionate2×

Product 1

HCID 540302272-(1-Methylethoxy)-2-oxoethyl 2-hydroxy-3-phenylpropionate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 6 mL aliquot of an ethyl ether solution containing 0.25M 2-chloroethyl 2-hydroxy-3-phenylpropionate, 0.25M isopropyl glycolate, and 1.0% tert-butylbenzene was added to 0.43 g Lipase AK. After mixing for 2 d at room temperature, the conversion of 2-chloroethyl 2-hydroxy-3-phenylpropionate to the title compound was estimated (by GC, Method B) to be approximately 28%. The GC peak assigned to the title compound was confirmed by HRMS: calcd for C13H14O5Tms (M-CH3) 323. 1314, obsd 323. 1290. In identical reactions substituting Lipase P30, Lipase G, Lipase MAP10, porcine pancreatic lipase, Lipase AP12 or Protease M for Lipase AK, the relative values for conversions at 2 d (Lipase AK=100) were 88, 85, 76, 51, 7, and 7%, respectively.

Workup

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

Sources & evidence

ORD record
ord-5b94bdcc06c74f06a02a0d03821608e0
Source dataset
uspto-grants-1994_12
Patent number
US05371001

Reaction notes

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