Isopropyl hydroxyacetate → 2-(1-Methylethoxy)-2-oxoethyl lactate

HRID 1491536Notes

Reaction equation

HRID 1491536 reaction equation
[C:1](OCCCl)(=[O:5])[CH:2]([CH3:4])[OH:3].[C:10]([O:14][CH:15]([CH3:17])[CH3:16])(=[O:13])[CH2:11][OH:12]>C(OCC)C>[C:1]([O:12][CH2:11][C:10]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13])(=[O:5])[CH:2]([CH3:4])[OH:3]

Participants

4

Reactant 2

HCID 69338Isopropyl hydroxyacetateHCID 189532282-Chloroethyl 2-hydroxypropanoate

Product 1

HCID 541539182-(1-Methylethoxy)-2-oxoethyl lactate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The efficacy of various enzyme preparations to catalyze the conversion of 0.25M 2-chloroethyl lactate and 0.25M isopropyl glycolate in ethyl ether to the title compound was determined after reaction for 24 hr with 0.5 g enzyme per 6.5 mL reaction mixture. Substituting Lipase AK, porcine pancreatic lipase, Lipase MAP10, Protease M, Lipase AP12, or Lipase G for Lipase P30, the relative values for conversion (Lipase P30=100) were 104, 44, 40, 36, 29 and 26, respectively. In each case substitution of acetonitrile for ethyl ether resulted in a slight reduction in the rate of reaction.

Sources & evidence

ORD record
ord-d7d4a86080f443619c79037a3abfef86
Source dataset
uspto-grants-1994_12
Patent number
US05371001

Reaction notes

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