3-Hydroxybenzaldehyde → 3-Benzyloxybenzaldehyde

HRID 1748995Notes

Reaction equation

HRID 1748995 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:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17].C(=O)([O-])[O-].[K+].[K+]>O.C(Cl)Cl>[CH2:4]([O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 6342AcetonitrileHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 743423-Benzyloxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In an acetonitrile (50 mL) solvent, benzyl bromide (4.6 mL, 38.68 mmol) was added to a solution including 3-hydroxybenzaldehyde (5.0 g, 40.94 mmol) and potassium carbonate (8.49 g, 61.43 mmol), and the reaction mixture was refluxed for 3 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 Compound 107b.

Workup

  1. temperaturethe reaction mixture was refluxed for 3 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-fc949b5154fc4f49adbea7f8a53ed3d2
Source dataset
uspto-grants-2015_10
Patent number
US09155690B2

Reaction notes

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