3-Hydroxybenzaldehyde → 3-Benzyloxybenzaldehyde

HRID 1504583Notes

Reaction equation

HRID 1504583 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=[O:14].C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>C(#N)C.O>[CH2:1]([O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 6344DichloromethaneHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 743423-BenzyloxybenzaldehydeYield 103.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

In 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. The filtrate was evaporated, and water was added to the resultant solid. The solid was filtered and washed with water to obtain Compound 123a (8.53 g, 98%).

Workup

  1. temperaturethe reaction mixture was refluxed for 3 hours
  2. temperatureAfter cooling
  3. customAn organic layer was dried
  4. filtrationfiltered
  5. customThe 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-bb6eaa84b169440ea6f4eca46c35b8dc
Source dataset
uspto-grants-2015_12
Patent number
US09216148B2

Reaction notes

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