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

HRID 2399511Notes

Reaction equation

HRID 2399511 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[CH2:12][CH:13]=[CH2:14].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 939882Methyl 3-allyl-4-hydroxybenzoate

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 (Example 42, Step B) 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 more 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 more acetone and dichloromethane
  3. customAfter removing the solvents
  4. distillationthe resulting oil was distilled under high vacuum

Sources & evidence

ORD record
ord-b22475391e1f49d4aac5b3d4c518fd03
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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