Water → 3,4,5,6-Tetrakis[(naphthalen-2-yl)oxy]benzene-1,2-dicarbonitrile

HRID 1457232Notes

Reaction equation

HRID 1457232 reaction equation
C(C1C(Cl)=C(Cl)C(Cl)=C(Cl)C=1C#N)#N.[C:15]([C:17]1[C:22]([O:23][C:24]2[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=2)=[C:21]([O:34][C:35]2[CH:44]=[CH:43][C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:36]=2)[C:20]([O:45][C:46]2[CH:55]=[CH:54][C:53]3[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=3)[CH:47]=2)=[C:19]([O:56][C:57]2[CH:66]=[CH:65][C:64]3[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=3)[CH:58]=2)[C:18]=1[C:67]#[N:68])#[N:16].C(=O)([O-])[O-].[K+].[K+].C1C2C(=CC=CC=2)C=CC=1O.O>CN(C)C=O>[C:67]([C:18]1[C:19]([O:56][C:57]2[CH:66]=[CH:65][C:64]3[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=3)[CH:58]=2)=[C:20]([O:45][C:46]2[CH:55]=[CH:54][C:53]3[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=3)[CH:47]=2)[C:21]([O:34][C:35]2[CH:44]=[CH:43][C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:36]=2)=[C:22]([O:23][C:24]2[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=2)[C:17]=1[C:15]#[N:16])#[N:68]

Participants

6

Reactant 4

HCID 962WaterHCID 86632-NaphtholHCID 11430Potassium CarbonateHCID 86753409HCID 86753409, compound

Product 1

HCID 221040573,4,5,6-Tetrakis[(naphthalen-2-yl)oxy]benzene-1,2-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Preparation of 1,2-dicyano-3,4,5,6-tetra(2-naphthoxy)benzene 1,2-Dicyano-3,4,5,6-tetrachlorobenzene (30.5 parts), potassium carbonate (62.8 parts) and 2-naphthol (98.1 parts) were stirred in dimethylformamide (140 parts) at 70° C. for 3 hours. The mixture was poured into water (300 parts) and extracted with chloroform (3×300 parts). The combined chloroform extracts were washed with dilute aqueous sodium hydroxide solution (500 parts) and then with water (500 parts). The chloroform was dried over anhydrous magnesium sulphate before evaporating under reduced pressure to leave a brown liquid which crystallised on adding butan-1-ol, cooling and standing for 2 hours. The crystallised solid was filtered, washed with butan-1-ol until the filtrates were colourless. The solid was dried to give 1,2-dicyano-3,4,5,6-tetra(2-naphthoxy)benzene (40.6 parts), m.p. 188°-190° C.

Workup

  1. extractionextracted with chloroform (3×300 parts)
  2. washThe combined chloroform extracts were washed with dilute aqueous sodium hydroxide solution (500 parts)
  3. dry with materialThe chloroform was dried over anhydrous magnesium sulphate
  4. custombefore evaporating under reduced pressure
  5. customto leave a brown liquid which
  6. customcrystallised
  7. additionon adding butan-1-ol
  8. temperaturecooling
  9. filtrationThe crystallised solid was filtered
  10. washwashed with butan-1-ol until the filtrates
  11. customThe solid was dried

Sources & evidence

ORD record
ord-1b0abd7aba734dbe832a9f2b78d5424e
Source dataset
uspto-grants-1998_12
Patent number
US05847114

Reaction notes

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