Ethanol → HCID 54264942, compound

Participants

Reaction Conditions

Reaction Steps

A dry 25 ml two-necked round bottom flask was equipped with a stirring bar, addition funnel, reflux condenser and nitrogen bubbler. The flask was charged with absolute ethanol (9.2 gm, 200 mmoles) and the addition funnel charged with thionyl chloride (4.3 gm, 36 mmoles). The flask and its contents were cooled to about 0° C. The thionyl chloride was added dropwise while maintaining the flask temperature at 5° C. or below. After the addition was completed, the resulting mixture was stirred for 1 hour at 0° C. Beta-chloroethylideneaminooxyacetic acid (2.7 gm, 18 mmoles) was added in one portion. The resulting mixture was allowed to warm to room temperature during 1 hour. The flask was warmed to 40°-45° C. and maintained for 4 hours. The resulting mixture was cooled, then solvents were removed in vacuo. The residue was taken up in ethyl acetate which was extracted with an aqueous solution of sodium bicarbonate. The ethyl acetate layer was dried over magnesium sulfate, filtered, then taken to "dryness" in vacuo. A brown oil (2.1 gm) was obtained. Distillation at 0.5 mm Hg gave the desired product as a clear oil (2.0 gm), b.p. 60°-70° C.

Provenance & Evidence