4-Hydroxybenzaldehyde → 4-[(4-Methylbenzyl)oxy]benzaldehyde

HRID 973391Notes

Reaction equation

HRID 973391 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[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1>C(C(C)=O)C>[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 77224-Methylbenzyl chlorideHCID 11430Potassium Carbonate

Product 1

HCID 5705874-[(4-Methylbenzyl)oxy]benzaldehydeYield 52.8%

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 23.2 g of α-chloro-p-xylene are added thereto. The resulting mixture is refluxed for 10 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 17.9 g of 4-(4-methylbenzyloxy)benzaldehyde in the form of white crystal.

Workup

  1. temperatureThe resulting mixture is refluxed for 10 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-8f3ff4292c9b4a57884ddc638228f6a2
Source dataset
uspto-grants-1991_11
Patent number
US05063197

Reaction notes

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