Tert-Butylbenzene → HCID 53924236, compound

HRID 1656714Notes

Reaction equation

HRID 1656714 reaction equation
OC(CC)[C:3]([O:5][CH2:6]CCl)=[O:4].[C:11]([O:15][CH3:16])(=[O:14])[CH2:12][OH:13].[C:17](C1C=CC=CC=1)(C)(C)[CH3:18]>C(OCC)C>[OH:13][CH:12]([CH2:17][CH3:18])[C:11]([O:15][CH2:16][C:3]([O:5][CH3:6])=[O:4])=[O:14]

Participants

5

Reactant 3

HCID 7366Tert-ButylbenzeneHCID 66774Methyl GlycolateHCID 18953223HCID 18953223, compound2×

Product 1

HCID 53924236HCID 53924236, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 6 mL aliquot of an ethyl ether solution containing 0.25 M 2-chloroethyl 2-hydroxybutyrate, 0.25 M methyl glycolate, and 0.125% tert-butylbenzene was added to 0.43 g Lipase AK. After mixing for 48 hr at room temperature, the conversion of 2-chloroethyl 2-hydroxybutyrate to the title compound was estimated (by GC, Method A) to be 43%. The GC peak assigned to the title compound was confirmed by HRMS: calcd for C6H8O5TMS (M--CH3) 233.0845, obsd 233.0878. In identical reactions substituting Lipase P30, Lipase G, or porcine pancreatic lipase for Lipase AK, the relative values for conversions at 48 hr (Lipase AK=100) were 81, 71, and 48, respectively.

Workup

  1. additionwas added to 0.43 g Lipase AK
  2. additionAfter mixing for 48 hr at room temperature

Sources & evidence

ORD record
ord-634805c0c82240e98e94f9e143928857
Source dataset
uspto-grants-1993_10
Patent number
US05254718

Reaction notes

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