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

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 -60QC 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.

1. additionThe reaction mixture became cloudy white during addition
2. stirringThe heterogeneous reaction mixture was stirred at -60QC for 30 min
3. washthe organic layer was washed with H2O (500 mL), brine (500 mL)
4. dry with materialdried over MgSO4
5. customEvaporation

ORD record

ord-00a31f0a07d84a3aa846c852ad7e7511

Source dataset

uspto-grants-1998_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05712396