Potassium Carbonate → Ethyl 2-[4-(4-chloroanilinomethyl)phenoxy]-2-methylpropionate

HRID 2058072Notes

Reaction equation

HRID 2058072 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([NH:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Br[C:18]([CH3:25])([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C(C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:18]([CH3:25])([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:10][CH:9]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 43212004-[(4-Chloroanilino)methyl]phenol

Product 1

HCID 20329838Ethyl 2-[4-(4-chloroanilinomethyl)phenoxy]-2-methylpropionateYield 55.1%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 500 mg of 4-(4-chloroanilinomethyl)phenol, 632 mg of ethyl 2-bromo-2-methylpropionate, 7.5 ml of methyl isobutyl ketone and 448 mg of potassium carbonate is refluxed under heating for 6 hours. The insolubles are filtered off from the reaction mixture, and the filtrate is washed with water, dried and concentrated. The residue (730 mg) is purified by column chromatography, using 22 g of silica gel and chloroform as a developer to give 410 mg of ethyl 2-[4-(4-chloroanilinomethyl)phenoxy]-2-methylpropionate, mp 58° to 60° C.

Workup

  1. temperatureis refluxed
  2. temperatureunder heating for 6 hours
  3. filtrationThe insolubles are filtered off from the reaction mixture
  4. washthe filtrate is washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue (730 mg) is purified by column chromatography

Sources & evidence

ORD record
ord-0404e23f4bff4955b605f66392ad303e
Source dataset
uspto-grants-1980_07
Patent number
US04214094

Reaction notes

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