(E)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate → (E)-3-methyl-5-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)-2-pentenyl acetate

Participants

Reaction Steps

A solution of 3.83 g (12 mmol) of (E)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate in acetonitrile (50 ml) was treated dropwise at 0° C. with a solution of ceric ammonium nitrate (16.4 g; 30 mmol) in water (50 ml). After completion of the addition the mixture was stirred for a further 20 minutes and diluted with water and chloroform. The organic phase was separated, washed with water, dried and concentrated to a yellow oil, yielding (E)-3-methyl-5-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)-2-pentenyl acetate (3.27 g).

Provenance & Evidence