Réaction #73709

Équation de réaction

p-cresol

benzoyl chloride

hydrochloric acid

→

p-tolyl benzoate

Rendement 92.0%

Solvants

pyridine

Conditions de réaction

Traitement

1. 1
   Températurewas refluxed for 1.5 hr
2. 2
   ExtractionThe product was extracted with 2×100 mL of diethyl ether
3. 3
   Extractionthe combined extract
4. 4
   Lavagewas washed by 2% NaOH
5. 5
   Séchagedried over Na2SO4
6. 6
   Autreevaporated to dryness
7. 7
   AutreDrying of the residue in vacuum

Mode opératoire

A mixture of 65.0 g (0.60 mol) of p-cresol, 92.7 g (0.66 mol) of benzoyl 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 diethyl ether, the combined extract was washed by 2% NaOH, then dried over Na2SO4, and evaporated to dryness. Drying of the residue in vacuum gave 117 g (92%) of p-tolyl benzoate (bp 127-135° C./25 mm Hg). A mixture of 117 g (0.552 mol) of p-tolyl benzoate and 92.0 (0.689 mol) of AlCl3 was slowly heated to 120-125° C. This mixture was stirred for 1 hr, and then 1000 mL of 2M HCl was added at 0° C. The product was extracted with 3×200 mL of diethyl ether, the combined extracts dried over Na2SO4 and then evaporated to dryness. This procedure gave 116 g (99%) of the 31 which was further used without an additional purification.

Source