Hydroquinone → Benzaldehyde, 4,4'-[1,4-phenylenebis(oxy)]bis-

HRID 2351792Notes

Reaction equation

HRID 2351792 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[C:7]1([CH:14]=[CH:13][C:11]([OH:12])=[CH:10][CH:9]=1)[OH:8].F[C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1>CC(N(C)C)=O>[C:11]1([O:12][C:7]2[CH:14]=[CH:13][C:11]([CH:1]=[O:4])=[CH:10][CH:9]=2)[CH:13]=[CH:14][C:7]([O:8][C:16]2[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 3813603Benzaldehyde, 4,4'-[1,4-phenylenebis(oxy)]bis-Yield 131.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

There was added 41.5 grams (0.30 mole) of anhydrous potassium carbonate to a solution of 11 grams (0.10 mole) of hydroquinone, 24.8 grams (0.20 mole) of 4-fluorobenzaldehyde and 200 ml of dimethylacetamide. The resulting solution was heated at reflux for 12 hours. The reaction mixture was then decanted from the insoluble potassium salts and allowed to cool. The cooled solution was added to water to effect precipitation of product which was isolated by filtration. The product was recrystallized from isopropanol/water to yield 21 grams (66%) of 4,4'[1,4-phenylenebis(oxy)]bisbenzaldehyde having a melting point of 157°-158° C. The identity of the product was further confirmed by proton NMR.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 12 hours
  3. customThe reaction mixture was then decanted from the insoluble potassium salts
  4. temperatureto cool
  5. additionThe cooled solution was added to water
  6. customprecipitation of product which
  7. customwas isolated by filtration
  8. customThe product was recrystallized from isopropanol/water

Sources & evidence

ORD record
ord-2832d4cddda6429fadc9a164b565c8b4
Source dataset
uspto-grants-1989_10
Patent number
US04873371

Reaction notes

Loading…