Phenol → 4,5-Diphenoxy-1,2-benzenedicarbonitrile

HRID 250476Notes

Reaction equation

HRID 250476 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:11]#[N:12])[C:5](=[CH:8][C:9]=1Cl)[C:6]#[N:7].[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:20](=[O:23])([O-])[O-].[K+].[K+]>CS(C)=O>[O:19]([C:2]1[CH:3]=[C:4]([C:11]#[N:12])[C:5](=[CH:8][C:9]=1[O:23][C:20]1[CH:4]=[CH:3][CH:2]=[CH:9][CH:8]=1)[C:6]#[N:7])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 8537474,5-Dichlorophthalonitrile

Product 1

HCID 6803274,5-Diphenoxy-1,2-benzenedicarbonitrileYield 90.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

5.0 g of 4,5-dichlorophthalonitrile was dissolved in 50 ml of DMSO. 14.3 g of phenol was added and the solution was heated to 90° C. Portions of 6.9 g of potassium carbonate was added every five minutes until a total of 55.2 g had been added. The mixture was stirred at 90° C. for thirty minutes then cooled and poured into 500 ml of ice-water. The resulting solid precipitate was collected and crystallized from methanol to produce 3.6 g of product; 1H NMR (200 Mz, CDCl3) δ=7.49-7.38 (m, 4H), 7.32-7.25 (m, 2H), 7.15 (s, 2H), 7.10-7.02 (m, 4H)

Workup

  1. additionhad been added
  2. temperaturethen cooled
  3. customThe resulting solid precipitate was collected
  4. customcrystallized from methanol

Sources & evidence

ORD record
ord-6aa6fe3895774b89959b1bc9d826a323
Source dataset
uspto-grants-2011_01
Patent number
US07863292B2

Reaction notes

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