Hydroquinone → Bis[4-(4-hydroxyphenoxy)phenyl]methanone

HRID 874860Notes

Reaction equation

HRID 874860 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[C:9](=[O:12])([O-])[O-].[K+].[K+].CC(N(C)C)=[O:17].F[C:22]1[CH:36]=[CH:35][C:25]([C:26]([C:28]2[CH:33]=[CH:32][C:31](F)=[CH:30][CH:29]=2)=[O:27])=[CH:24][CH:23]=1.[C:37]1(C)[CH:42]=[CH:41]C=[CH:39][CH:38]=1>O>[OH:2][C:1]1[CH:8]=[CH:7][C:5]([O:6][C:22]2[CH:36]=[CH:35][C:25]([C:26]([C:28]3[CH:33]=[CH:32][C:31]([O:17][C:37]4[CH:42]=[CH:41][C:9]([OH:12])=[CH:39][CH:38]=4)=[CH:30][CH:29]=3)=[O:27])=[CH:24][CH:23]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 785HydroquinoneHCID 1140TolueneHCID 95824,4'-DifluorobenzophenoneHCID 11430Potassium CarbonateHCID 31374Dimethylacetamide

Product 1

HCID 18914770Bis[4-(4-hydroxyphenoxy)phenyl]methanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

In a 2-liter four-necked flask equipped with a condenser tube, a Dean-Stark apparatus and a nitrogen blowing tube, 66.07 g (600 mmol) of hydroquinone, 91.22 g (660 mmol) of potassium carbonate, 500 mL of dimethylacetamide and 260 mL of toluene were mixed. The mixture was heated to 120° C. with stirring under nitrogen stream and was refluxed for 4 hours for removal of the solvent and the water content in the raw materials. The reaction solution was cooled down to room temperature and was subsequently heated at 135° C. for 24 hours after addition of 6.55 g (30 mmol) of 4,4′-difluorobenzophenone for removal of toluene. The reaction solution was kept heated for another 5 hours, was subsequently cooled down to room temperature and was added dropwise to 2.5 L of water. The resulting solid substance was filtered through filter paper having the mean pore size of 1 and was vacuum dried at 80° C. for 12 hours. The resulting dried solid matter was subjected to Soxhlet extraction using acetone for 6 hours. The acetone solution was further purified by a silica gel column (eluent: hexane/ethyl acetate=1.5/1), and 10.54 g of 4,4′-bis(4-hydroxyphenoxy)benzophenone was obtained.

Workup

  1. customIn a 2-liter four-necked flask equipped with a condenser tube
  2. temperaturewas refluxed for 4 hours for removal of the solvent
  3. temperatureThe reaction solution was cooled down to room temperature
  4. temperaturewas subsequently heated at 135° C. for 24 hours
  5. customfor removal of toluene
  6. temperatureThe reaction solution was kept heated for another 5 hours
  7. temperaturewas subsequently cooled down to room temperature
  8. additionwas added dropwise to 2.5 L of water
  9. filtrationThe resulting solid substance was filtered
  10. filtrationthrough filter paper
  11. customdried at 80° C. for 12 hours
  12. customThe resulting dried solid matter
  13. extractionwas subjected to Soxhlet extraction
  14. customfor 6 hours
  15. customThe acetone solution was further purified by a silica gel column (eluent: hexane/ethyl acetate=1.5/1)

Sources & evidence

ORD record
ord-cdf53674789c44009364267f6a6d9b40
Source dataset
uspto-grants-2015_03
Patent number
US08981035B2

Reaction notes

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