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

HRID 2254207Notes

Reaction equation

HRID 2254207 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>CN(C)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 92.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 200 ml of anhydrous dimethylformamide was dissolved 30.0 g of p-hydroxybenzaldehyde, and 40.9 g of anhydrous potassium carbonate was added to the solution and the mixture was stirred at room temperature for 30 minutes. Then, 46.3 g of benzyl bromide was dropped into the mixture and a reaction was carried out at room temperature with stirring overnight. After the reaction, the reaction mixture was extracted with diethyl ether, and the solvent was removed from the extract by distillation. The obtained residue was recrystallized from a mixed solvent of diethyl ether and n-hexane to obtain 48.2 g (yield=92.3%) of p-benzyloxybenzaldehyde in the form of a colorless prism.

Workup

  1. additionwas added to the solution
  2. customwas carried out at room temperature
  3. stirringwith stirring overnight
  4. customAfter the reaction
  5. extractionthe reaction mixture was extracted with diethyl ether
  6. customthe solvent was removed from the
  7. extractionextract by distillation
  8. customThe obtained residue was recrystallized from a mixed solvent of diethyl ether and n-hexane

Sources & evidence

ORD record
ord-3bd85410785648b0b877ca470eb3e725
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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