Benzyl Bromide → Methyl 2-(4-benzyloxyphenyl)acetate

HRID 1935218Notes

Reaction equation

HRID 1935218 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.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>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 2756645Methyl 2-(4-benzyloxyphenyl)acetateYield 92.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (4-hydroxy-phenyl)-acetic acid methyl ester (5.0 g, 30.0 mmol) and potassium carbonate (5.0 g, 36.1 mmol) in acetone (10 mL) was treated with benzyl bromide (4.29 mL, 36.1 mmol). The reaction mixture was then heated at 90° C. for 6 h. At this time, the potassium carbonate was removed by filtration. The filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 95/5 hexanes/ethyl acetate) afforded (4-benzyloxy-phenyl)-acetic acid methyl ester (7.1 g, 92.1%) as a clear oil: EI-HRMS m/e calcd for C16H16O3 (M+) 256.1099 found 256.1103.

Workup

  1. customAt this time, the potassium carbonate was removed by filtration
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e9236fac3fa048228ed68b61e3947765
Source dataset
uspto-grants-2002_05
Patent number
US06384220B2

Reaction notes

Loading…