Allyl bromide → Ethyl 3-{4-[(prop-2-en-1-yl)oxy]phenyl}propanoate

HRID 580950Notes

Reaction equation

HRID 580950 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[OH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[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]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:11]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 2736435Ethyl 4-hydroxyhydrocinnamate

Product 1

HCID 19348971Ethyl 3-{4-[(prop-2-en-1-yl)oxy]phenyl}propanoateYield 97.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Allyl bromide (2.30 g) was added to a stirred suspension of ethyl 3-(4-hydroxyphenyl)propionate (3.49 g) and anhydrous potassium carbonate (2.76 g) in butan-2-one (30 ml). The reaction mixture was heated at reflux for 18 hours. The reaction mixture was allowed to cool to ambient temperature and the mixture was filtered. The filtrate was evaporated to give an oil which was purified by column chromatography on silica gel (Merck.Art. No. 9385) using a 4:1 (v/v) mixture of n-hexane and ethyl acetate as eluent to give ethyl 3-(4-allyloxyphenyl)propionate (4.09 g) as a colourless oil; NMR (CDCl3): 1.22 (3H, t), 2.48 (2H, t), 2.88 (2H, t), 4.13 (2H, q), 4.51 (2H, m), 5.25-5.42 (2H, m), 5.95-6.15 (1H, m), 6.83 (2H, d) and 7.03 (2H, d); m/z 235 (M+H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 hours
  3. filtrationthe mixture was filtered
  4. customThe filtrate was evaporated
  5. customto give an oil which
  6. customwas purified by column chromatography on silica gel (Merck.Art
  7. additiona 4:1 (v/v) mixture of n-hexane and ethyl acetate as eluent

Sources & evidence

ORD record
ord-5a2bdee2237346168fe2f46f62cd61b0
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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