Reaktion #2250790

Reaktionsgleichung

methyl 4-chlorobutyrate

p-anilinophenol

potassium carbonate

→

methyl 4-(p-anilinophenoxy)butyrate

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONA mixture of 198 g
2. 2
   Sonstigeof the N,N-dimethylformamide was removed by distillation
3. 3
   workup.ADDITIONThe residue was poured into ice water
4. 4
   Extraktionthe resulting mixture was extracted with benzene
5. 5
   ExtraktionThe dried benzene extract
6. 6
   Sonstigewas chromatographed through a column of neutral alumina

Vorschrift

A mixture of 198 g. of methyl 4-chlorobutyrate, 269 g. of p-anilinophenol, and 636 g. of anhydrous potassium carbonate, all in 500 ml. of N,N-dimethylformamide was heated at 140° C. while stirring for 4 hours and about 300 ml. of the N,N-dimethylformamide was removed by distillation. The residue was poured into ice water and the resulting mixture was extracted with benzene. The dried benzene extract was chromatographed through a column of neutral alumina and the benzene solvent was stripped from the eluent leaving the product, methyl 4-(p-anilinophenoxy)butyrate, as a dark amber liquid. This ester was sufficiently pure to be used as an antioxidant. Crystallization of the crude ester from ethanol afforded a solid, mp. 40°-41° C.

Quelle