(Z)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate → (Z)-3-methyl-5-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadienyl)-2-pentenyl acetate

Participants

Reaction Conditions

Reaction Steps

A solution of (Z)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate (0.98 g) in acetonitrile (15 ml) was treated dropwise at -20° C. with a solution of ceric ammonium nitrate (4.1 g) in water (15 ml). After 15 minutes the mixture was warmed to -10° C and left at this temperature for 1 hour. The mixture was diluted with ice-water and extracted twice with methylene chloride. The extracts were washed with water, dried and chromatographed on silica gel with hexane/ethyl acetate 95:5, yielding 0.67 g of (Z)-3-methyl-5-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadienyl)-2-pentenyl acetate as a pale yellow oil.

Provenance & Evidence