Réaction #63131

Équation de réaction

hydrochloric acid

3-tetradecylphenol

acetate

aluminum chloride

→

desired compound

1-(2-Hydroxy-4-tetradecylphenyl)ethanone

Solvants

ether

Conditions de réaction

Traitement

1. 1
   Températureto cool
2. 2
   Extractionextracted several times with ether
3. 3
   Lavagewashed with water, brine
4. 4
   Autredried
5. 5
   AutreThe crude material was chromatographed on silica gel
6. 6
   Lavageeluting with hexane:ethyl acetate (50:1)

Mode opératoire

A 20 g portion of 3-tetradecylphenol, acetate was heated at 110° C. and 8.4 g of aluminum chloride was added in portions over a 3 hour period. The mixture was allowed to cool, then diluted with ether, poured onto ice containing 10 ml of concentrated hydrochloric acid and extracted several times with ether. The ether extracts were combined, washed with water, brine and dried. The crude material was chromatographed on silica gel, eluting with hexane:ethyl acetate (50:1), giving 15.8 g of the desired compound, mp 45°-46° C.

Source