Sodium Dithionite → (E)-5-(2,5-dihydroxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate

Participants

Reaction Steps

A solution of 3.27 g (11.3 mmol) of (E)-3-methyl-5-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)-2-pentenyl acetate in 60 ml of THF was treated dropwise with 40 ml of a freshly Prepared 0.5M sodium dithionite solution. After completion of the addition the mixture was diluted with water and extracted with chloroform. The combined extracts were washed with water and freed from solvent. The solid residue was washed with hexane and dried under oil pump vacuum, yielding 2.94 g of (E)-5-(2,5-dihydroxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate as a colourless powder; m.p. 94.5°-96° C.

Provenance & Evidence