Diphenyl Ether → Methyl 2,2-dimethyl-3-(3-allyl-4-hydroxyphenyl)propionate

Participants

Reaction Steps

A solution of methyl 2,2-dimethyl-3-(4-allyloxyphenyl)propionate (1.56 g) in diphenyl ether was heated at reflux for 15 minutes. The reaction mixture was cooled to ambient temperature and the reaction mixture was filtered through a silica gel pad. Elution with a 4:1 (v/v) mixture of hexane and ethyl acetate gave methyl 2,2-dimethyl-3-(3-allyl-4-hydroxyphenyl)propionate (1.53 g) as a yellow oil; microanalysis, found: C, 72.2; H, 7.80%; C15H20O3 requires: C, 72.6; H, 8.12%; NMR(CDCl3): 1.15(6H,s), 2.73(2H,s), 3.35(2H,m), 3.63(3H,s), 4.87(1H,s), 5.10(2H,m), 5.95(1H,m), 6.67(1H,m) and 6.83(2H,m); m/z 249 (M+H).

Provenance & Evidence