Allyl bromide → Ethyl 4-(prop-2-en-1-yloxy)benzoate

HRID 256397Notes

Reaction equation

HRID 256397 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[CH:20]=[CH2:21]>CC(C)=O>[CH2:21]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1)[CH:20]=[CH2:19]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 8434EthylparabenHCID 11430Potassium Carbonate

Product 1

HCID 227685Ethyl 4-(prop-2-en-1-yloxy)benzoateYield 99.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 66.4 g (0.4 mole) ethyl 4-hydroxybenzoate in 100 ml acetone, under a nitrogen atmosphere was added 55.3 g (0.40 mole) finely powdered potassium carbonate and 53.2 g (0.44 mole) allyl bromide and the resulting mixture was heated at reflux overnight. After cooling to room temperature the mixture was filtered, washing with ethyl ether. The filtrate and washings were washed with water, brine and dried (MgSO4). Evaporation of solvent in vacuo gave 82.3 g of product as a clear oil. 1H-NMR(CDCl3)ppm(delta): 5.0-5.5 (m), 5.8 (m), 6.8 (m), 8.0 (m).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux overnight
  3. filtrationwas filtered
  4. washwashing with ethyl ether
  5. washThe filtrate and washings were washed with water, brine
  6. dry with materialdried (MgSO4)
  7. customEvaporation of solvent in vacuo

Sources & evidence

ORD record
ord-7cd2c42fe4e6498987a82a3b80f58c4a
Source dataset
uspto-grants-1987_10
Patent number
US04703052

Reaction notes

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