Tert-Butylbenzene → 2-(1-Methylethoxy)-2-oxoethyl 2-hydroxy-2-phenylacetate

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[OH:1][CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3](OCCCl)=[O:4].[C:15]([O:19][CH:20]([CH3:22])[CH3:21])(=[O:18])[CH2:16][OH:17].C(C1C=CC=CC=1)(C)(C)C>C(OCC)C>[OH:1][CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:17][CH2:16][C:15]([O:19][CH:20]([CH3:22])[CH3:21])=[O:18])=[O:4]

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실험 절차

A 6 mL aliquot of an ethyl ether solution containing 0.25 M 2-chloroethyl 2-hydroxy-2-phenylacetate, 0.25 M isopropyl glycolate, and 1.0% tert-butylbenzene was added to 0.43 g Lipase P30. After mixing for 5 d at room temperature, the conversion of 2-chloroethyl 2-hydroxy-2-phenylacetate to the title compound was estimated (by GC, Method B) to be approximately 15%. The GC peak assigned to the title compound was confirmed by HRMS: calcd for C12H12O5Tms (M--CH3) 309.1158, obsd 309.1171. In identical reactions substituting Lipase G, Lipase AK, Lipase MAP10, Protease M, Lipase AP12, or porcine pancreatic lipase for Lipase P30, the relative values for conversions at 5 d (Lipase P30 =100) were 17, 12, 12, 6, 4, and 2%, respectively.