Benzyl Bromide → 3-Benzyloxy-4-methoxybenzaldehyde

HRID 613035Notes

Reaction equation

HRID 613035 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:5]([OH:6])[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[CH2:18]([O:6][C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][C:7]=1[O:8][CH3:9])[CH:2]=[O:1])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=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 isovanillin (200 g) in dimethylformamide (500 ml) is added potassium carbonate (236 g) under ice-cooling, and thereto is added dropwise benzyl bromide (203 ml), and the mixture is stirred overnight. The insoluble materials in the resulting residue are removed by filtration, and washed with acetone, and the filtrate is concentrated under reduced pressure to remove the solvent. The residue is washed again with ether and water, and concentrated under reduced pressure to remove the solvent to give 3-benzyloxy-4-methoxybenzaldehyde as an oily product.

Workup

  1. temperaturecooling
  2. customThe insoluble materials in the resulting residue are removed by filtration
  3. washwashed with acetone
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customto remove the solvent
  6. washThe residue is washed again with ether and water
  7. concentrationconcentrated under reduced pressure
  8. customto remove the solvent

Sources & evidence

ORD record
ord-277e0e9eb5074a76b09fd7116039aed8
Source dataset
uspto-grants-1999_12
Patent number
US06005106

Reaction notes

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