Dimethylformamide → HCID 21218080, compound

HRID 1586250Notes

Reaction equation

HRID 1586250 reaction equation
[N+]([C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=1)[C:8]#[N:9])([O-])=O.[C:14]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:19]=1[OH:28])([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[C:24]([C:20]1[CH:21]=[C:22]([C:4]2[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=2)[C:8]#[N:9])[CH:23]=[C:18]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:19]=1[OH:28])([CH3:27])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 314052,6-Di-tert-butylphenolHCID 974431,2-Benzenedicarbonitrile, 4-nitro-

Product 1

HCID 21218080HCID 21218080, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 4-nitrophthalonitrile (8 g, 0.05 mol) was added 2,6 di-tert-butylphenol (11.44 g, 0.06 mol), potassium carbonate (9 g, 0.07 mol) and DMF (50 ml), producing a deep red colour. The reaction mixture was stirred under a nitrogen atmosphere for 72 h. Water (300 ml) was added and the mixture extracted with ethyl acetate (3×100 ml), the organic layer was further washed with water (3×75 ml) and dried over MgSO4. Evaporation of the solvent under reduced pressure yielded the crude product. Recrystallisation from ethanol yielded the pure product 4-(3,5-di-tert-butyl-4-hydroxyphenyl)phthlonitrile (1) as colourless, prismatic crystals (18.70 g, 81.70%), m.p. 209-210° C.; IR (KBr) 3416 (OH), 2231 (CN) cm- 1; (Found C, 79.55%; H, 7.50%; N, 8.20%. C22H24N2O requires C, 79.47%; H, 7.28%; N, 8.43%.); MS (EI) m/e 332 (M+); δH (200 MHz, solvent CDCl3): 1.51 (18H, s), 5.55 (1H, s), 7.39 (2H, s), 7.75-8.00 (3H, m).

Workup

  1. customproducing a deep red colour
  2. extractionthe mixture extracted with ethyl acetate (3×100 ml)
  3. washthe organic layer was further washed with water (3×75 ml)
  4. dry with materialdried over MgSO4
  5. customEvaporation of the solvent under reduced pressure
  6. customyielded the crude product
  7. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-c8327fd19f56405098496dc33f5ce243
Source dataset
uspto-grants-1999_08
Patent number
US05942612

Reaction notes

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