Catechol → HCID 14116725, compound

HRID 277315Notes

Reaction equation

HRID 277315 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1([C:9](=[CH:11][CH:12]=[CH:13][CH:14]=1)[OH:10])[OH:8].[C:15]1([CH3:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.F[C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=1.CC([N:34](C)C)=O>>[C:9]1([O:10][C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=2)[C:7]([O:8][C:18]2[CH:19]=[CH:20][C:15]([C:21]#[N:34])=[CH:16][CH:17]=2)=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 5

HCID 289CatecholHCID 1140TolueneHCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 31374Dimethylacetamide

Product 1

HCID 14116725HCID 14116725, compoundYield 86%

Procedure

A suspension of potassium carbonate (26.5 g, 192 mmol) and catechol (10.63 g, 96.54 mmol) in dimethylacetamide (600 mL) containing toluene (100 mL) was refluxed using Dean-stark apparatus. After 3 h, para-fluorobenzonitrile (23.4 g, 193 mmol) was added and reaction was continued for 24 h. Upon cooling, the reaction mixture was evaporated. The organic product was dissolved in ethyl acetate and filtered through Celite. Evaporation of the solution gave a solid which after recrystallization from ethanol gave 4,4′-(1,2-benzenedioxy)dibenzonitrile (26 g), 86% yield, mp=112.5° C.

Workup

  1. temperaturewas refluxed
  2. customreaction
  3. waitwas continued for 24 h
  4. temperatureUpon cooling
  5. customthe reaction mixture was evaporated
  6. dissolutionThe organic product was dissolved in ethyl acetate
  7. filtrationfiltered through Celite
  8. customEvaporation of the solution
  9. customgave a solid which
  10. customafter recrystallization from ethanol

Sources & evidence

ORD record
ord-ce9ddb4597cb460ea45c912177e674bd
Source dataset
uspto-grants-2002_03
Patent number
US06355765B1

Reaction notes

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