3,5-Di-tert-butyl-4-hydroxybenzaldehyde → dihydro-4-[(3,5-di-tert-butyl-4-hydroxyphenyl)hydroxymethyl]-2-isopropyl-2H-1,2-oxazin-3(4H)-one

Participants

Reaction Steps

A stirred mixture of 1.1 g (5 mmol) dihydro-4-bromo-2-isopropyl-2H-1,2-oxazin-3(4H)-one, 1.2 g (5 mmol) of 3,5-di-tert-butyl-4-hydroxybenzaldehyde and 1 g of zinc dust in 20 ml of benzene were refluxed for 15 hours and concentrated. The concentrate was taken up in methylene chloride and chromatographed on silica gel with 30% ethyl acetate-hexane to yield 1.2 g of dihydro-4-[(3,5-di-tert-butyl-4-hydroxyphenyl)hydroxymethyl]-2-isopropyl-2H-1,2-oxazin-3(4H)-one, mp 150°-153° C.

Provenance & Evidence