4-Hydroxybenzaldehyde → 4-[(3-Chlorophenyl)methoxy]benzaldehyde

HRID 973392Notes

Reaction equation

HRID 973392 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20]Cl>C(C(C)=O)C>[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 12103m,alpha-Dichlorotoluene

Product 1

HCID 7354654-[(3-Chlorophenyl)methoxy]benzaldehydeYield 88.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

18.3 g of p-hydroxybenzaldehyde is dissolved in 200 ml of methyl ethyl ketone, and then 22.8 g of potassium carbonate and 24.2 g of m-chlorobenzyl chloride are added thereto. The resulting mixture is refluxed for 8 hours in a stream of nitrogen. Insoluble substances produced are removed by filtration, and then the solvent is distilled away. The resulting residue is distilled under reduced pressure to obtain 32.6 g of 4-(3-chlorobenzyloxy)benzaldehyde in the form of white crystal.

Workup

  1. temperatureThe resulting mixture is refluxed for 8 hours in a stream of nitrogen
  2. customInsoluble substances produced
  3. customare removed by filtration
  4. distillationthe solvent is distilled away
  5. distillationThe resulting residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-078a98a913304fd1865101b59fb60f94
Source dataset
uspto-grants-1991_11
Patent number
US05063197

Reaction notes

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