Dimethyl Sulfoxide → HCID 88537164, compound

Participants

Reaction Steps

A solution of dimethyl sulfoxide (1.17 g, 15 mmol) in dichloromethane (50 mL) is cooled to −30° C. and treated with oxalyl chloride (1.92 g, 15 mmol). The reaction mixture is then treated with 10-hydroxydecanoic acid (2.06 g, 10 mmol) in dichloromethane (50 mL) and allowed to warm to room temperature over a period of 2 h. The reaction is then washed with water (2×50 mL). The organic layer is dried over sodium sulfate and then treated with hydroxylamine hydrochloride (1.03 g 15 mmol) and sodium hydroxide (0.6 g in 10 mL water) and stirred vigorously for 1 h. The organic phase is then separated dried over sodium sulfate and concentrated in vacuo to give 11[(E)-hydroxyimino-decanoic acid (1.8 g, 9.0 mmol).

Provenance & Evidence