3-Hydroxybenzaldehyde → 3-Benzyloxybenzaldehyde

HRID 338807Notes

Reaction equation

HRID 338807 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-e6e17fce2b804c54a43541bfe260fcdc
Source dataset
uspto-grants-2014_11
Patent number
US08889881B2

Reaction notes

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