Acetic Acid → 2-Cyclohexene-1,4-diyl Diacetate

Participants

Reaction Steps

Lit., J. Org. Chem., 49:4619 (1984). To a stirred solution of 2.8 g (12.5 mmol) palladium acetate, 27.2 g (267 mmol) lithium acetate, and 7.64 g (70.7 mmol) benzoquinone in 200 ml acetic acid at room temperature were added 26.1 g (300 mmol) manganese dioxide and a solution of 23.8 ml (250 mmol) 1,3-cyclohexadiene in 400 ml pentane, and stirring continued for 16 h. The two-phase reaction mixture was separated and the acetic acid phase extracted twice with pentane. The combined organic extracts were washed successively with saturated brine, water, and 2 M sodium hydroxide solution, then the organic phases were dried over sodium sulphate and concentrated in vacuo. Recrystallisation from pentane afforded 16.1 g (33%) of the title compound as an off-white crystalline solid. MS m/e (%): 138 ([M−AcOH]+, 8), 96 ([M−AcOH—COCH2]+, 100), 43 (40).

Provenance & Evidence