Water → Benzaldehyde, 4-(phenylmethoxy)-

HRID 1748994Notes

Reaction equation

HRID 1748994 reaction equation
[C:1](#N)[CH3:2].[CH2:4](Br)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:12](=[O:15])([O-])[O-].[K+].[K+].C(Cl)Cl.[OH2:21]>>[CH2:4]([O:21][C:2]1[CH:1]=[CH:7][C:6]([CH:12]=[O:15])=[CH:5][CH:4]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 6344DichloromethaneHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-Yield 88.7%

Procedure

In an acetonitrile (30 mL) solvent, benzyl bromide (1.95 mL, 16.40 mmol) was added to a solution including 4-hydroxybenzaldhehyde (2.0 g, 16.38 mmol) and potassium carbonate (3.40 g, 24.60 mmol), and then, the reaction mixture was refluxed for 1.5 hours. After cooling, the reaction mixture was distributed between methylene chloride and water. An organic layer was dried by using MgSO4, and filtered. A filtrate was evaporated, and water was added to the resultant solid. The solid was filtered and washed with water to obtain 4-(benzyloxy)benzaldehyde (3.082 g, 88.7%).

Workup

  1. temperaturethe reaction mixture was refluxed for 1.5 hours
  2. temperatureAfter cooling
  3. customAn organic layer was dried
  4. filtrationfiltered
  5. customA filtrate was evaporated
  6. additionwater was added to the resultant solid
  7. filtrationThe solid was filtered
  8. washwashed with water

Sources & evidence

ORD record
ord-a7b4619a81244805ba862b8d6ce9c8eb
Source dataset
uspto-grants-2015_10
Patent number
US09155690B2

Reaction notes

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