Catechol → HCID 14116725, compound

HRID 439571Notes

Reaction equation

HRID 439571 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])O.[N+]([C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1)([O-])=O.[C:20](=[O:23])([O-])[O-].[K+].[K+]>CS(C)=O>[C:5]1([O:23][C:20]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[CH:6]=[CH:7][CH:8]=[CH:1][C:3]=1[O:4][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 289CatecholHCID 11430Potassium CarbonateHCID 120904-Nitrobenzonitrile

Product 1

HCID 14116725HCID 14116725, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4,4'-(o-phenylenedioxy)dibenzonitrile was prepared from catechol (11.0 g., 0.100 mol.), 4-nitrobenzonitrile (32.56 g., 0.220 mol.), and anhydrous potassium carbonate (82.8 g., 0.600 mol.) in 300 mL of anhydrous dimethyl sulfoxide 80° C. for 20 h. It was obtained as white crystals, m.p. 117°-118° C., after recrystallization from isopropanol and heptane. IR spectrum (KBr pellet, cm-): 3100, 3065 (aromatic C-H), 2232 (C≡N), 1584, 1497 (aromatic C=C), 1270 (arylether).

Workup

  1. customIt was obtained as white crystals, m.p. 117°-118° C.
  2. customafter recrystallization from isopropanol and heptane

Sources & evidence

ORD record
ord-2399a51d7330450d8ae8697c042650c6
Source dataset
uspto-grants-1996_05
Patent number
US05514769

Reaction notes

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