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

HRID 1613045Notes

Reaction equation

HRID 1613045 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-dihydroxy-benzoate, 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-4480b7be219548a98298cea90032a915
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

Loading…