Water → 3-Phenoxyphthalonitrile

HRID 2631

Reaction equation

HRID 2631 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+]([O-])=O)[C:4]=1[C:12]#[N:13])#[N:2].[O-:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Na+].O>CN(C)C=O>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:4]=1[C:12]#[N:13])#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 1626521,2-Benzenedicarbonitrile, 3-nitro-HCID 4445035Phenolate Sodium

Product 1

HCID 8536913-PhenoxyphthalonitrileYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1,2-dicyano-3-nitrobenzene (2.77 parts) and sodium phenoxide (2.79 parts) in dimethylformamide (50 parts) was stirred at 120° C. for 2 hours. The reaction mixture was poured into water and extracted with diethyl ether (100 parts). The diethyl ether extract was washed with 5% aqueous potassium hydroxide solution (2×200 parts) and water (2×200 parts) and the diethyl ether was removed under reduced pressure to leave a solid. Recrystallisation of the solid from a 1:1 diethyl ether:petroleum spirit (b.pt.60°-80° C.) gave 1,2-dicyano-3-phenoxybenzene (2.1 parts, 60%) as a pale green solid, m.pt.110°-112° C.

Workup

  1. extractionextracted with diethyl ether (100 parts)
  2. extractionThe diethyl ether extract
  3. washwas washed with 5% aqueous potassium hydroxide solution (2×200 parts) and water (2×200 parts)
  4. customthe diethyl ether was removed under reduced pressure
  5. customto leave a solid
  6. customRecrystallisation of the solid from a 1:1 diethyl ether

Sources & evidence

ORD record
ord-50d21924746f443faec1be54b17f257d
Source dataset
uspto-grants-1998_03
Patent number
US05730759

Linked notes

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