Allyl bromide → Methyl 2-hydroxy-4-[(prop-2-en-1-yl)oxy]benzoate

HRID 1494217Notes

Reaction equation

HRID 1494217 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:13](Br)[CH:14]=[CH2:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[CH:9][C:10]([O:12][CH2:15][CH:14]=[CH2:13])=[CH:11][C:2]=1[OH:1]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 16523Methyl 2,4-Dihydroxybenzoate

Product 1

HCID 13019278Methyl 2-hydroxy-4-[(prop-2-en-1-yl)oxy]benzoateYield 67%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 102 g (0.607 mol) of methyl 2,4-dihydroxybenzoate, 54 mL (0.619 mol) of allyl bromide and 126 g (0.91 mol) of anhydrous potassium carbonate in 300 mL of anhydrous acetone was stirred at reflux for 3 hours. The reaction mixture was filtered and the solid was washed with acetone. After removal of the acetone from the filtrate under reduced pressure, the residue was distilled to give 85 g (67% yield), bp 106°-108°/0.3 mm of 2-hydroxy-4-(2-propenyloxy)benzoic acid methyl ester.

Workup

  1. temperatureat reflux for 3 hours
  2. filtrationThe reaction mixture was filtered
  3. washthe solid was washed with acetone
  4. customAfter removal of the acetone from the filtrate under reduced pressure
  5. distillationthe residue was distilled

Sources & evidence

ORD record
ord-f3f556dad4ef49dbb705dd980bf1d9d1
Source dataset
uspto-grants-1991_06
Patent number
US05025036

Reaction notes

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