Acetic Anhydride → 3-(4-Acetoxy-3,5-di-tert-butylphenyl)-l-(tetrahydropyran-2-yloxy)propane

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Reaction Steps

A vigourously stirred mixture of 40.74 g (0.117 mol) of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-(tetrahydropyran-2-yloxy)propane and 5.85 g (16.7 mmol) of tetrabutylammonium hydrogen sulphate in 250 ml of dichloromethane and 250 ml of 50% aqueous sodium hydroxide is treated at 0° C. dropwise with 14.32 g (0.140 mol) of acetic anhydride, dissolved in 100 ml of dichloromethane, under a nitrogen atmosphere. After addition is complete, the mixture is reacted for an additional 4--hour period at ambient temperature. Following usual extradtive work-up, 42.69 g (93%) of 3-(4-acetoxy-3,5-di-tert-butylphenyl)-l-(tetrahydropyran-2-yloxy)propane is obtained as a brown viscous liquid, which is used for the following deprotection step without further purification. (C24H38O4 ; F.W. 390.6).

Provenance & Evidence