Reaction #73704

Reaction equation

p-cresol

acetyl chloride

hydrochloric acid

→

p-tolyl acetate

Yield 93.0%

Solvents

pyridine

Conditions

Workup

1. 1
   Temperaturewas refluxed for 1.5 h
2. 2
   ExtractionThe product was extracted with 2×100 mL of diethyl ether
3. 3
   Extractionthe combined extract
4. 4
   Washwas washed with 2% NaOH
5. 5
   Dryingdried over Na2SO4
6. 6
   Otherevaporated to dryness
7. 7
   OtherDrying the residue in vacuum

Procedure

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 h and then added to 600 mL of 2% hydrochloric acid. The product was extracted with 2×100 mL of diethyl ether, the combined extract was washed with 2% NaOH, then dried over Na2SO4, and 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 heated to 120-125° C. for 30 min. The mixture was stirred 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 gave 39.7 g (99%) of the title product which was further used without an additional purification.

Source