Ethyl Acrylate → Ethyl 3-(m-bromophenoxy)propionate

HRID 37402Notes

Reaction equation

HRID 37402 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9]([O:13][CH2:14][CH3:15])(=[O:12])[CH:10]=[CH2:11]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:11][CH2:10][C:9]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 8821Ethyl AcrylateHCID 115633-Bromophenol

Product 1

HCID 19935504Ethyl 3-(m-bromophenoxy)propionateYield 52.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 20 g of 3-bromophenol, 92 g of ethyl acrylate and 1.8 ml of Triton B (35% in methanol) was boiled at reflux overnight. After distilling off the excess acrylate at normal pressure, the residue was distilled in a high vacuum. There were obtained 16.7 g of ethyl 3-(m-bromophenoxy)propionate as a colorless oil, boiling point 107°-110° C./67 Pa.

Workup

  1. temperatureat reflux overnight
  2. distillationAfter distilling off the excess acrylate at normal pressure
  3. distillationthe residue was distilled in a high vacuum

Sources & evidence

ORD record
ord-cb1e6fa4699944a0843587f423d8b69a
Source dataset
uspto-grants-1995_05
Patent number
US05420273

Reaction notes

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