Potassium Carbonate → Methyl 4-(p-anilinophenoxy)butyrate

HRID 2163608Notes

Reaction equation

HRID 2163608 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].[NH:9]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH:9]([C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])=[CH:20][CH:21]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 312084-HydroxydiphenylamineHCID 76612Butanoic acid, 4-chloro-, methyl ester

Product 1

HCID 22750429Methyl 4-(p-anilinophenoxy)butyrate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  1. additionA mixture of 198 g
  2. customof the N,N-dimethylformamide was removed by distillation
  3. additionThe residue was poured into ice water
  4. extractionthe resulting mixture was extracted with benzene
  5. extractionThe dried benzene extract
  6. customwas chromatographed through a column of neutral alumina

Sources & evidence

ORD record
ord-8c938eb0faa6449a80e2df5904495f8e
Source dataset
uspto-grants-1979_01
Patent number
US04136044

Reaction notes

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