Allyl bromide → Ethyl 4-allyloxyphenoxyacetate

HRID 580952Notes

Reaction equation

HRID 580952 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[OH:5][C:6]1[CH:18]=[CH:17][C:9]([O:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:17][CH:18]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 13187337Ethyl 2-(4-hydroxyphenoxy)acetate

Product 1

HCID 53873708Ethyl 4-allyloxyphenoxyacetateYield 103.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Allyl bromide (3.37 g) was added to a stirred suspension of ethyl 4-hydroxyphenoxyacetate (5.14 g) [prepared by method of Moser, J.A.C.S., (1950), 72, 1413) and potassium carbonate (3.90 g) in butan-2-one (50 ml). The reaction mixture was heated at reflux for 12 hours. The reaction mixture was cooled to ambient temperature and then filtered. The filtrate was evaporated to give an oil which was purified by column chromatography on silica gel (Merck. Art. No. 7734) using a 4:1 (v/v) mixture of hexane and ethylacetate as eluent to give ethyl 4-allyloxyphenoxyacetate (6.41 g) as a colourless oil; microanalysis, found: C, 65.8; H, 7.20%; C13H16O4 requires C, 66.1; H, 6.83%; NMR (CDCl3): 1.28 (3H, t), 4.25 (2H, q), 4.48 (2H, m), 4.57 (2H, s), 5.22-5.44 (2H, m), 5.92-6.12 (1H, m) and 6.84 (4H, s).

Workup

  1. customprepared by method of Moser, J.A.C.S
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 12 hours
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. customto give an oil which
  7. customwas purified by column chromatography on silica gel (Merck
  8. additiona 4:1 (v/v) mixture of hexane and ethylacetate as eluent

Sources & evidence

ORD record
ord-19a47b178a944d3e98b86aa96bbe3444
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

Loading…