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

HRID 338806Notes

Reaction equation

HRID 338806 reaction equation
C(#N)C.[CH2:4](Br)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>O.C(Cl)Cl>[CH2:4]([O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 6342AcetonitrileHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In an acetonitrile (30 mL) solvent, benzyl bromide (1.95 mL, 16.40 mmol) was added to a solution including 4-hydroxybenzaldehyde (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-26828b8da679450ca455c224426de343
Source dataset
uspto-grants-2014_11
Patent number
US08889881B2

Reaction notes

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