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

関与物質

反応手順

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 twophase 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).

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