Dimethyl Sulfoxide → HCID 54571041, compound

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (0.46 mL, 5.25 mmol) was added dropwise to a solution of dimethyl sulfoxide (0.88 mL, 12.50 mmol) dissolved in dichloromethane (40 mL). The mixture was cooled to −78° C. and allowed to stir for 1 hour. A solution of (3-hydroxymethyl-2-methylphenoxy)acetic acid tert-butyl ester (1.26, 5.00 mmol) in dichloromethane was cannulated into the reaction mixture and allowed to stir at −78° C. for an additional hour. Triethylamine (3.49 mL, 25 mmol) was added. The reaction mixture was allowed to warm to room temperature, poured into water, and the layers were separated. The aqueous layer was extracted twice with dichloromethane. The combined organic extracts were washed with 2N hydrochloric acid and saturated sodium bicarbonate, dried over anhydrous sodium sulfate, and concentrated in vacuo. Purification by silica gel chromatography, eluting with hexane/acetone, gave (3-formyl-2-methylphenoxy)acetic acid tert-butyl ester as a slightly yellow crystalline solid (1.07 g, 85.9%).

Provenance & Evidence