Benzyl Bromide → Methyl 5-(benzyloxy)-2-hydroxybenzoate

HRID 1644580Notes

Reaction equation

HRID 1644580 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[CH2:19]([O:12][C:9]1[CH:10]=[CH:11][C:2]([OH:1])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 75077Methyl Gentisate

Product 1

HCID 13026913Methyl 5-(benzyloxy)-2-hydroxybenzoateYield 63%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixed solution of methyl 2,5-dihydroxybenzoate (10.0 g), potassium carbonate (12.3 g) and acetone (100 ml) was added benzyl bromide (7.43 ml), and the mixture was stirred overnight at room temperature. After the insoluble material was removed by filtration, the mother solution was concentrated. The obtained residue was purified by column chromatography (LL, Biotage cartridge, ethyl acetate:n-hexane=1:9→1:5) to give methyl 5-benzyloxy-2-hydroxybenzoate (9.63 g, 63%) as colorless crystals.

Workup

  1. customAfter the insoluble material was removed by filtration
  2. concentrationthe mother solution was concentrated
  3. customThe obtained residue was purified by column chromatography (LL, Biotage cartridge, ethyl acetate:n-hexane=1:9→1:5)

Sources & evidence

ORD record
ord-91cbb4ad27b24cb2a13388a0a6c33f60
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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