Benzyl Bromide → 3-Benzyloxy-4-methoxybenzaldehyde

HRID 2236660Notes

Reaction equation

HRID 2236660 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:12]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 12127Isovanillin

Product 1

HCID 806713-Benzyloxy-4-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxy-4-methoxybenzaldehyde (5.0 g, 33 mmol) in N,N-dimethylformamide (165 mL) is added benzyl bromide (4.3 mL, 36 mmol), followed by potassium carbonate (˜325 mesh, 14 g, 100 mmol). The reaction mixture is stirred for 4 hours at room temperature and then partitioned between diethyl ether and water. The aqueous phase is extracted with ether (3×50 mL). The combined ethereal extracts were washed twice with water and once with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give 3-benzyloxy-4-methoxybenzaldehyde as golden oil, which crystallized upon standing to afford a white solid. The material is used in the following step without further purification.

Workup

  1. custompartitioned between diethyl ether and water
  2. extractionThe aqueous phase is extracted with ether (3×50 mL)
  3. washThe combined ethereal extracts were washed twice with water and once with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6a3e68499729419ba20d1ae7080db780
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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