3,4-Dihydroxybenzaldehyde → 3,4-Bis[(3,4-dichlorophenyl)methoxy]benzaldehyde

HRID 485771Notes

Reaction equation

HRID 485771 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1O)[CH:5]=[O:6].[C:11](=[O:14])([O-])[O-].[K+].[K+].[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:21]Br>CC(C)=O>[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:21][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:14][CH2:11][C:23]1[CH:20]=[CH:19][C:18]([Cl:17])=[C:25]([Cl:26])[CH:24]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 6397264-(Bromomethyl)-1,2-dichlorobenzene

Product 1

HCID 202479363,4-Bis[(3,4-dichlorophenyl)methoxy]benzaldehydeYield 84.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2 g of 3,4-dihydroxybenzaldehyde in 40 ml of acetone, were added 4.40 g of anhydrous potassium carbonate and 6.24 g of 3,4-dichlorobenzyl bromide. The mixture was refluxed for 24 hours. The reaction mixture was then removed of the acetone by distillation under reduced pressure, admixed with 200 ml of water, and the intended product was extracted with 200 ml of chloroform. The chloroform layer was dried over anhydrous sodium sulfate, and stripped of the chloroform by distillation under reduced pressure to precipitate white crystals. The raw crystals were recrystallized from ethyl alcohol to give 4.99 g of colorless crystals having a melting point of 181°-183° C. The IR absorption spectrum of the compound, as measured in KBr-tablet, showed the following absorption maxima (in wave number, cm-1) 658, 693, 710, 760, 795, 805, 830, 875, 1030, 1135, 1168, 1200, 1245, 1280, 1370, 1403, 1437, 1460, 1470, 1510, 1585, 1600, 1690, 2730, 2830, 2870, 2910, and 3070.

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. customThe reaction mixture was then removed of the acetone by distillation under reduced pressure
  3. extractionthe intended product was extracted with 200 ml of chloroform
  4. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  5. distillationstripped of the chloroform by distillation under reduced pressure
  6. customto precipitate white crystals
  7. customThe raw crystals were recrystallized from ethyl alcohol

Sources & evidence

ORD record
ord-ead68e3688074f0d9b967b9bccc884a3
Source dataset
uspto-grants-1985_08
Patent number
US04537880

Reaction notes

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