Hydrochloric Acid → 4,4'-Bis(3,4-dicyanophenoxy)biphenyl

HRID 279924Notes

Reaction equation

HRID 279924 reaction equation
[C:1]1(O)[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[N+]([C:18]1[CH:19]=[C:20]([C:26]#[N:27])[C:21](=[CH:24][CH:25]=1)[C:22]#[N:23])([O-])=O.[C:28](=[O:31])([O-])[O-].[K+].[K+].Cl>CS(C)=O>[C:26]([C:20]1[CH:19]=[C:18]([CH:25]=[CH:24][C:21]=1[C:22]#[N:23])[O:13][C:10]1[CH:11]=[CH:12][C:7]([C:4]2[CH:5]=[CH:6][C:1]([O:31][C:28]3[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[C:20]([C:26]#[N:27])[CH:19]=3)=[CH:2][CH:3]=2)=[CH:8][CH:9]=1)#[N:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 71124,4'-DihydroxybiphenylHCID 11430Potassium Carbonate2×HCID 974431,2-Benzenedicarbonitrile, 4-nitro-

Product 1

HCID 6348834,4'-Bis(3,4-dicyanophenoxy)biphenylYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture containing 4,4'-biphenol 2 (5.0 g, 0.027 mol), 4-nitrophthalonitrile 3 (9.7 g, 0.056 mol) and anhydrous potassium carbonate (9.6 g, 0.070 mol) in 60 ml of dry dimethyl sulfoxide was stirred at room temperature for 24 hours. The potassium carbonate was added in three portions. At this point, the reaction mixture was slowly poured into cold, dilute hydrochloric acid (200 ml). The crude precipitate was isolated by suction filtration, washed with water until neutral and dried. Purification was achieved by recrystallization from acetone-water to afford 11.2 g (95%) of 1, m.p. 232°-235° C.

Workup

  1. customThe crude precipitate was isolated by suction filtration
  2. washwashed with water until neutral and
  3. customdried
  4. customPurification
  5. customwas achieved by recrystallization from acetone-water

Sources & evidence

ORD record
ord-15a34c8d078940158a390a95b5af6b17
Source dataset
uspto-grants-1986_05
Patent number
US04587325

Reaction notes

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