Hydrochloric Acid → 4-Methylphenyl acetate

Participants

Reaction Steps

A mixture of 65.0 g (0.60 mol) of p-cresol, 51.8 g (0.66 mol) of acetyl chloride, and 6 mL of anhydrous pyridine was refluxed for 1.5 hr and then added to 600 mL of 2% hydrochloric acid. The product was extracted with 2×100 mL of ether, the combined extract was washed with 2% NaOH, then dried over Na2SO4, and finally evaporated to dryness. Drying the residue in vacuum gave 83.7 g (93%) of p-tolyl acetate (bp 104-105° C./25 mm Hg). A mixture of 40.0 g (0.27 mol) of p-tolyl acetate and 45.0 (0.34 mol) of AlCl3 was slowly (for ca. 0.5 hr) heated to 120-125° C. This mixture was stirred at this temperature for 1 hr, and then 500 mL of 2M HCl was added at 0° C. The product was extracted with 3×100 mL of diethyl ether, the combined extract was dried over Na2SO4 and then evaporated to dryness. This procedure gave 39.7 g (99%) of the title product which was further used without an additional purification.

Provenance & Evidence