Benzyl Bromide → Methyl 3-(benzyloxy)-5-hydroxybenzoate

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].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:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Procedure

A mixture of 8.40 g (0.05 mmol) methyl 3,5-dihydroxybenzoate (159) and 7.60 g (0.055 mmol) of potassium carbonate in 250 mL of acetone was stirred at room temperature for 30 min. Then 8.55 g (0.05 mmol) of benzyl bromide dissolved in 100 mL of acetone was added. The suspension was refluxed for 24 h. The solid was filtered, and the filtrate was evaporated. The residue was purified by column chromatography (SiO2, CH2Cl2/EtOAc=9/1) to give 160.