Dimethyl Sulfoxide → HCID 14742766, compound

Participants

Reaction Steps

A solution of dimethylsulfoxide (0.54 mL) in dry dichloromethane (3 mL) was added with stirring to a chilled (<-60° C.) solution of oxalyl chloride (0.59 mL) in dry dichloromethane (15 mL) at such a rate that the reaction temperature did not exceed -60° C. After 15 minutes a solution of 1-butyl-5-methoxy-2-naphthalenemethanol (1.54 g) in dichloromethane (6 mL) was added while the reaction temperature was still maintained below -60° C. The reaction was allowed to proceed for 15 minutes then triethylamine (2.9 mL) was added to the chilled reaction and, after an additional 20 minutes the cooling bath was removed and the mixture was allowed to equilibrate to room temperature. After 2N hydrochloric acid (225 mL) was added, the layers were separated and the aqueous phase was extracted with dichloromethane (50 mL), then the combined organic extracts were dried (MgSO4) and evaporated to yield 1.6 g of 1-butyl-5 -methoxy-2-naphthalenecarboxaldehyde. Sublimation of a portion (50° C.; 0.1 mm) furnished the analytical sample, mp 61.5°-62.5° C. Anal. Calcd for C16H18O2 : C, 79.31; H, 7.49 Found: C, 79.02; H, 7.53

Provenance & Evidence