Allyl bromide → 4-Allyloxy-3-allylbenzoic acid methyl ester

HRID 1741739Notes

Reaction equation

HRID 1741739 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH:12]=[CH:13][CH3:14].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[CH:22]=[CH2:23]>CC(C)=O>[CH2:12]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[O:1][CH2:23][CH:22]=[CH2:21])[C:6]([O:8][CH3:9])=[O:7])[CH:13]=[CH2:14]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 54233466Methyl 4-hydroxy-3-propenylbenzoate

Product 1

HCID 112417484-Allyloxy-3-allylbenzoic acid methyl esterYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 3.04 g (15.8 mmol) of methyl 4-hydroxy-3-propenylbenzoate (prepared by the procedure described in patent application WO91/11999) was refluxed with anhydrous potassium carbonate (4.37 g, 2 equiv) and allyl bromide (3.5 mL, 2.5 equiv) in acetone overnight. The mixture was filtered through celite and the filter cake was washed with acetone and dichloromethane. After removing the solvents, the resulting oil was distilled under high vacuum to give 3.2 g (87%) of the title compound.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washthe filter cake was washed with acetone and dichloromethane
  3. customAfter removing the solvents
  4. distillationthe resulting oil was distilled under high vacuum

Sources & evidence

ORD record
ord-4222048740394ce7bc3aa7ccdba5268b
Source dataset
uspto-grants-1994_08
Patent number
US05334598

Reaction notes

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