Benzyl Bromide → 3-Benzyloxy-4-methoxybenzaldehyde

HRID 324038Notes

Reaction equation

HRID 324038 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-93cbcf96a740455cbc0fef588f44ea0f
Source dataset
uspto-grants-2001_04
Patent number
US06214996B1

Reaction notes

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