Benzyl Bromide → HCID 21840988, compound

Reaction equation

[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7])=[O:2].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:6]([O:8][CH3:9])=[O:7])=[O:2]

Participants

Procedure

To a solution of methyl 3-formyl-4-hydroxybenzoate (3.55 g, 19.7 mmol) in DMF (20 ml) was added benzyl bromide (3.70 g, 21.67 mmol) and K2CO3 (4.1 g, 29.6 mmol). The reaction was stirred at ambient temperature overnight and the solvent evaporated to dryness (at reduced pressure). The residue was partitioned between ethyl ether and water and the aqueous layer extracted a second time with ethyl ether. The organic extracts were combined, washed with brine, dried (MgSO4 ) and evaporated to give methyl 3-formyl-4-benzyloxybenzoate as an off-white solid which was used without further purification.