Dimethyl Sulfoxide → 10-Undecenal

Participants

Reaction Steps

Under an argon atmosphere, a stirred solution of 82.0 grams (0.646 mole) of oxalyl chloride in 600 ml of methylene chloride was cooled to -50° to -60° C., and a solution of 100.9 grams (1.292 moles) of dimethyl sulfoxide in 120 ml of methylene chloride was added dropwise during a 10-15 minute period. The reaction mixture temperature was maintained at -50° to -60° C. during the addition. Upon completion of addition, the reaction mixture was stirred for two minutes, and then a solution of 100.0 grams (0.587 mole) of 10-undecen-1-ol in 130 ml of methylene chloride was added dropwise during a 15 minute period while maintaining the reaction mixture temperature at -50° to -60° C. Upon completion of addition, the reaction mixture was stirred for 15 minutes, and then 297.1 grams (2.936 moles) of triethylamine was added dropwise during a five minute period while still maintaining the reaction mixture temperature at -50° to -60° C. Upon completion of addition, the reaction mixture was stirred as it was allowed to warm to ambient temperature. After this time 700 ml of water was stirred with the reaction mixture. The water layer was separated and washed with two 160 ml portions of methylene chloride. The washes were combined with the organic layer, and the combination was washed with three 160 ml portions of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and was then filtered. The filtrate was concentrated under reduced pressure to an oil/solid residue. The residue was stirred with 400 ml of pentane, and the solid was separated by filtration. The filtrate was concentrated under reduced pressure yielding 101.4 grams of 10-undecenal as an oil. The ir spectrum was consistent with the proposed structure.

Provenance & Evidence