4-Hydroxybenzaldehyde → Benzaldehyde, 4-(phenylmethoxy)-

HRID 1354885Notes

Reaction equation

HRID 1354885 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(C)=O>[CH2:16]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-Yield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Hydroxybenzaldehyde of the formula (7) (100 g), potassium carbonate (226 g) and acetone (500 ml) were taken in a reaction flask and stirred for 15 minutes. Benzylbromide (154 g) was then added at room temperature and the reaction mass was stirred at the same temperature for a period of 8–10 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was dumped into ice water and extracted with toluene. The combined organic extracts were washed with 10% aq. sodium hydroxide solution followed by water. The solvent was removed under reduced pressure and the resulting residue was triturated with pet. ether to afford 4-benzyloxybenzaldehyde of the formula (8) (160–165 g, 93–95%).

Workup

  1. stirringthe reaction mass was stirred at the same temperature for a period of 8–10 h
  2. customAfter completion of the reaction
  3. extractionextracted with toluene
  4. washThe combined organic extracts were washed with 10% aq. sodium hydroxide solution
  5. customThe solvent was removed under reduced pressure
  6. customthe resulting residue was triturated with pet. ether

Sources & evidence

ORD record
ord-68e1aea8ca4048179aa16c65ecbe0caf
Source dataset
uspto-grants-2007_05
Patent number
US07223881B2

Reaction notes

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