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

HRID 1033618Notes

Reaction equation

HRID 1033618 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>[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH2:15][CH:14]=[CH2:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

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]benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 2,4-dihydroxybenzoate (25 g, 148.7 mmol), allyl bromide (18.2 g, 150 mmol), and potassium carbonate (30.8 g, 22.3 mmol) were added to about 250 ml of acetone and the reaction mixture was refluxed with stirring overnight. The reaction mixture was filtered and concentrated. Separation of the pure compound was achieved by chromatography on silica gel using a Waters Prep 500™ and a 20% ethyl acetate/80% hexane solvent system.

Workup

  1. temperaturethe reaction mixture was refluxed
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. customSeparation of the pure compound

Sources & evidence

ORD record
ord-8d94f03318c34ebda671578f4f9c2cc4
Source dataset
uspto-grants-1994_05
Patent number
US05310951

Reaction notes

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