Benzyl Bromide → 3-Benzyloxy-4-methoxybenzaldehyde

HRID 1420774Notes

Reaction equation

HRID 1420774 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[CH:19]=[O:20]>CO>[CH2:7]([O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[CH:19]=[O:20])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 12127Isovanillin

Product 1

HCID 806713-Benzyloxy-4-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.2 equivalents of K2CO3 and 1.2 equivalents of benzyl bromide are added to a suspension of 0.33 mol of 3-hydroxy-4-methoxybenzaldehyde in 400 ml of methanol. After 24 hours' reflux, the reaction mixture is filtered while hot and the organic phase is then evaporated off under reduced pressure. The isolated residue is taken up in 300 ml of chloroform and then washed with water. After extraction, drying and filtration, evaporating off the organic phase under reduced pressure allows the expected product to be isolated.

Workup

  1. temperatureAfter 24 hours' reflux
  2. filtrationthe reaction mixture is filtered while hot and the organic phase
  3. customis then evaporated off under reduced pressure
  4. washwashed with water
  5. extractionAfter extraction
  6. customdrying
  7. filtrationfiltration
  8. customevaporating off the organic phase under reduced pressure
  9. customto be isolated

Sources & evidence

ORD record
ord-f4c6219de9e84d3e88e847785f4c6db4
Source dataset
uspto-grants-2000_06
Patent number
US06071945

Reaction notes

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