Tert-Butylbenzene → 2-Methoxy-2-oxoethyl lactate

HRID 1656708Notes

Reaction equation

HRID 1656708 reaction equation
[C:1]([O:6][CH2:7]CCl)(=[O:5])C(C)O.[C:10]([O:14][CH3:15])(=[O:13])[CH2:11][OH:12].[C:16](C1C=CC=CC=1)(C)(C)C>C(OCC)C>[C:10]([O:14][CH2:15][C:1]([O:6][CH3:7])=[O:5])(=[O:13])[CH:11]([CH3:16])[OH:12]

Participants

5

Reactant 3

HCID 7366Tert-ButylbenzeneHCID 66774Methyl GlycolateHCID 189532282-Chloroethyl 2-hydroxypropanoate2×

Product 1

HCID 197888162-Methoxy-2-oxoethyl lactate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 6.5 mL aliquot of an ethyl ether solution containing 0.25 M 2-chloroethyl lactate (prepared as described in Example 1a), 0.25 M methyl glycolate, and 0.125% tert-butylbenzene was added to 0.5 g Lipase P30. After mixing for 48 hr at room temperature, the conversion of 2-chloroethyl lactate to the title compound was estimated (by GC, Method A) to be 40%. In identical reactions substituting Lipase AK, Lipase G, Lipase MAP10, Protease M, Lipase AP12, or porcine pancreatic lipase for Lipase P30, the relative values for conversions at 48 hr (Lipase P30 =100) were 101, 90, 44, 43, 32, and 13, respectively.

Workup

  1. additionwas added to 0.5 g Lipase P30
  2. additionAfter mixing for 48 hr at room temperature

Sources & evidence

ORD record
ord-cea88ec20f05449b9aa3ef31450eff7d
Source dataset
uspto-grants-1993_10
Patent number
US05254718

Reaction notes

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