Dimethyl Sulfoxide → (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienal

Participants

Reaction Steps

To a CH2Cl2 solution (15 mL) of oxalyl chloride (7.81 mL, 87.7 mmol) was added dimethyl sulfoxide (12.5 mL, 175.4 mmol) dropwise over 30 min at -60° C. The resulting clear solution was stirred at this temperature for 20 min. A solution of trans, trans-farnesol (Aldrich Chemical Co.) (15 g, 67.5 mmol) in CH2Cl2 (325 mL) was added dropwise over 15 min. The reaction mixture became cloudy white during addition. The heterogeneous reaction mixture was stirred at -60° C. for 30 min, whereupon triethylamine (56.4 mL, 405 mmol) was added dropwise over 10 min. The reaction mixture became thick. The reaction mixture was allowed to warm to RT over 1 h. Ethyl ether (800 mL) was added and the organic layer was washed with H2O (500 mL), brine (500 mL) and dried over MgSO4. Evaporation gave 15 g (100%) of title compound as a crude oil.

Provenance & Evidence