2,4-Dihydroxybenzaldehyde → 4-Benzyloxy-2-hydroxybenzaldehyde

HRID 397304Notes

Reaction equation

HRID 397304 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:11]([O:10][C:8]1[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([OH:1])[CH:9]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 72132,4-DihydroxybenzaldehydeHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 5612354-Benzyloxy-2-hydroxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

13.8 g (0.1 mol) 2,4-dihydroxybenzaldehyde are dissolved in 150 ml acetone, 17.1 g (0.1 mol) benzylbromide and 13.8 g (0.1 mol) potassium carbonate are added, and the mixture is stirred at room temperature for 3 d. After filtration, the solvent is removed in vacuo and the residual crude product further purified by column chromatography on silica gel using dichloromethane as eluent.

Workup

  1. filtrationAfter filtration
  2. customthe solvent is removed in vacuo
  3. customthe residual crude product further purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-18617ac054bb42f287216936d8a4275d
Source dataset
uspto-grants-2003_08
Patent number
US06610687B1

Reaction notes

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