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

HRID 5928Notes

Reaction equation

HRID 5928 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 (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-02742acc49b343f1b44fb58c1729b32d
Source dataset
uspto-grants-1993_09
Patent number
US05246944

Reaction notes

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