Benzyl Bromide → Methyl 3-(benzyloxy)-4-methoxybenzoate

HRID 2108885Notes

Reaction equation

HRID 2108885 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.[C:14]([O:25][CH3:26])(=[O:24])[C:15]1[CH:23]=[CH:22][C:19]([O:20][CH3:21])=[C:17]([OH:18])[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C)C=O.O>[CH2:14]([O:8][C:7]1[CH:9]=[CH:10][C:2]([C:1]([O:12][CH3:13])=[O:11])=[CH:3][C:4]=1[O:5][CH3:6])[C:15]1[CH:23]=[CH:22][CH:19]=[CH:17][CH:16]=1.[CH2:33]([O:18][C:17]1[CH:16]=[C:15]([CH:23]=[CH:22][C:19]=1[O:20][CH3:21])[C:14]([O:25][CH3:26])=[O:24])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

8

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 19844Methyl VanillateHCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

Product 2

HCID 4171221Methyl 3-(benzyloxy)-4-methoxybenzoateHCID 5059267Methyl 4-(benzyloxy)-3-methoxybenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl vanillate or methyl isovanillate (7.29 g, 40 mmol) in dimethylformamide (25 mL), potassium carbonate (8.29 g, 60 mmol) and benzyl bromide (5.26 mL, 44 mmol) were added. The mixture was heated to 100° C. for 3 h. After cooling to r.t., water was added and the product was extracted several times with ethyl acetate. The combined organic phases were washed with water and brine. After drying over Na2SO4, the solvent was removed to yield methyl 4-benzyloxy-3-methoxybenzoate or methyl 3-benzyloxy-4-methoxybenzoate, respectively, quantitatively, which was used without further purification.

Workup

  1. temperatureAfter cooling to r.t.
  2. extractionthe product was extracted several times with ethyl acetate
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialAfter drying over Na2SO4
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-ddab9e05afdd475297bedf707f315db0
Source dataset
uspto-grants-2009_04
Patent number
US07514460B2

Reaction notes

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