Tert-Butylbenzene → HCID 54181210, compound

HRID 1491544Notes

Reaction equation

HRID 1491544 reaction equation
OC(C(C)C)[C:3]([O:5][CH2:6]CCl)=[O:4].[C:12]([O:16][CH3:17])(=[O:15])[CH2:13][OH:14].[C:18](C1C=CC=CC=1)(C)([CH3:20])[CH3:19]>C(OCC)C>[OH:14][CH:13]([CH:18]([CH3:20])[CH3:19])[C:12]([O:16][CH2:17][C:3]([O:5][CH3:6])=[O:4])=[O:15]

Participants

5

Reactant 3

HCID 7366Tert-ButylbenzeneHCID 66774Methyl GlycolateHCID 18953225HCID 18953225, compound2×

Product 1

HCID 54181210HCID 54181210, compound

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-methylbutyrate, 0.25M methyl glycolate, and 1.0% tert-butylbenzene was added to 0.40 g Lipase P30. After mixing for 10 d at room temperature, the conversion of 2-chloroethyl 2-hydroxy-3-methylbutyrate to the title compound was estimated (by GC, Method A) to be <20%. The GC peak assigned to the title compound was confirmed by HRMS: calcd for C7H10O5Tms (M-CH3) 247.1001, obsd 247.0973. In identical reactions substituting Lipase AK or porcine pancreatic lipase for Lipase P30, the relative values for conversions at 10 d (Lipase P30=100) were 33 and 0, respectively.

Workup

  1. additionwas added to 0.40 g Lipase P30
  2. additionAfter mixing for 10 d at room temperature

Sources & evidence

ORD record
ord-8f59e7a7bcb04394bba4b3285dbd3527
Source dataset
uspto-grants-1994_12
Patent number
US05371001

Reaction notes

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