Dimethyl Sulfoxide → Tetradecanal

Participants

Reaction Conditions

Reaction Steps

A solution of oxalylchloride (8.0 mL, 88.0 mmol, 2.2 eq.) in abs. dichloromethane (200 mL) was treated with DMSO (13.6 mL, 192 mmol, 4.8 eq.) at −60° C. After 3 min the reaction mixture was warmed to approx. 15° C. Then a solution of tetradecan-1-ol (8.56 g, 40.0 mmol) in dry dichloromethane (40 mL) and after further 3 min triethylamine (28 mL, 200 mmol, 5.0 eq.) were added. Then the reaction mixture was slowly warmed to 5° C. and quenched by addition of water (200 mL). The phases were separated and the aqueous phase was extracted with dichloromethane (3×100 mL). The combined organic phases were washed with brine (1×200 mL) and dried over MgSO4. The solvent was removed under reduced pressure and the product was isolated as a white solid, which was used in the next reaction without purification. Yield: 10.4 g (100%), purity: 98% (GC).

Provenance & Evidence