Acetyl chloride → HCID 13245938, compound

Participants

Reaction Steps

To 600 mL of toluene in a Morton reaction flask was added 100 g (0.598 mol) of 2-methyl-3-nitrophenylmethanol with stirring. The solution was heated to reflux, and 100 mL of toluene was removed by distillation into a Dean Stark trap. The solution was cooled, and 48.3 mL of pyridine was added. After further cooling with an ice-water bath, 51.6 g (0.658 mol) of acetyl chloride was added dropwise. Upon complete addition, the reaction mixture was allowed to warm to ambient temperature, and was stirred for 16 hours. The reaction mixture was heated under reflux for 3.5 hours, cooled to ambient temperature, then poured over 1 L of ice. When the ice had melted, the organic layer was separated, and the aqueous layer washed with three portions of 300 mL each of toluene. The toluene wash was combined with the organic layer, and the whole was washed with two portions of 250 mL each of aqueous 2 N hydrochloric acid, 250 mL of saturated aqueous solution of sodium chloride, two portions of 250 mL each of an aqueous 2 N solution of sodium hydroxide, and finally, 250 mL of a saturated aqueous solution of sodium chloride. The organic layer was dried with magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to give a residual oil. The oil was subjected to distillation using a Kugelrohr distilling system to give 107.3 g of 2-methyl-3-nitrophenylmethyl acetate, b.p. 120° C./0.25 mm.

Provenance & Evidence