Ethyl Bromide → methyl 3(E)-[4-ethoxy-3-propoxyphenyl]acrylate

HRID 987872Notes

Reaction equation

HRID 987872 reaction equation
[CH2:1](Br)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[OH:10][C:11]1[CH:22]=[CH:21][C:14](/[CH:15]=[CH:16]/[C:17]([O:19][CH3:20])=[O:18])=[CH:13][C:12]=1[O:23][CH2:24][CH2:25][CH3:26]>CC(=O)CC>[CH2:1]([O:10][C:11]1[CH:22]=[CH:21][C:14](/[CH:15]=[CH:16]/[C:17]([O:19][CH3:20])=[O:18])=[CH:13][C:12]=1[O:23][CH2:24][CH2:25][CH3:26])[CH3:2]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 22987074HCID 22987074, compound

Product 1

HCID 22987083methyl 3(E)-[4-ethoxy-3-propoxyphenyl]acrylate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

0.49 ml (6.60 mmol) of ethyl bromide and 1.37 g (9.9 mmol) of potassium carbonate are added to a mixture of 780 mg (3.30 mmol) of methyl (E)-4-hydroxy-3-propoxycinnamate and 10 ml of 2-butanone and then refluxed for 2 hours. Thereafter, the reaction mixture is cooled to room temperature and is partitioned between ethyl acetate and water, and the organic phase is washed several times with water, dried over magnesium sulfate, filtered and evaporated down. Chromatography of the residue over silica gel using 9:1 cyclohexane/ethyl acetate gives methyl 3(E)-[4-ethoxy-3-propoxyphenyl]acrylate.

Workup

  1. temperaturerefluxed for 2 hours
  2. customis partitioned between ethyl acetate and water
  3. washthe organic phase is washed several times with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated down

Sources & evidence

ORD record
ord-719c79daf1a94cbebeadbab72621b48e
Source dataset
uspto-grants-2003_10
Patent number
US06632909B2

Reaction notes

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