Benzyl Bromide → Methyl 4-(2-benzyloxybenzyl)benzoate

HRID 1982809Notes

Reaction equation

[OH:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C)C=O>[CH2:25]([O:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of methyl 4-(2-hydroxybenzyl)benzoate (1.5 g) and potassium carbonate (0.94 g) in N,N-dimethylformamide (200 mL) was added benzyl bromide (0.81 mL), and the mixture was stirred at 50° C. for 5 hours. In soluble material was removed by filtration, and to the filtrate was added water and dilute hydrochloric acid. The mixture was extracted with ethylacetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=4/1) to give methyl 4-(2-benzyloxybenzyl)benzoate (2.1 g).

Workup

customIn soluble material was removed by filtration
additionto the filtrate was added water and dilute hydrochloric acid
extractionThe mixture was extracted with ethylacetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was removed under reduced pressure
customthe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record: ord-15ebdf9acedd437c948b145477809b6a
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07541341B2

Reaction notes

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