Potassium Carbonate → 1,2-Bis-(3,4-dicyanophenoxy)-3,5-ditertiarybutylbenzene

HRID 1647907Notes

Reaction equation

HRID 1647907 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:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:22]=[C:20]([OH:21])[C:19]=1O)([CH3:17])([CH3:16])[CH3:15].[C:30](=[O:33])([O-])[O-].[K+].[K+]>CS(C)=O>[C:12]([C:6]1[CH:5]=[C:4]([CH:11]=[CH:10][C:7]=1[C:8]#[N:9])[O:21][C:20]1[CH:19]=[C:18]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:22]=1[O:33][C:30]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([C:12]#[N:13])[CH:5]=1)#[N:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 660993,5-Di-tert-butylcatecholHCID 974431,2-Benzenedicarbonitrile, 4-nitro-

Product 1

HCID 229064391,2-Bis-(3,4-dicyanophenoxy)-3,5-ditertiarybutylbenzeneYield 86.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3.60 g (0.02 moles plus 0.14 g excess) of 4-nitrophthalonitrile was dissolved in 50 ml anhydrous DMSO in a 100 ml three-necked flask fitted with a magnetic stirrer bar, nitrogen-gas inlet and thermometer. 2.22 g (0.01 moles) of 3,5-ditertiarybutylcatechol (supplied by Fluka) was added to the mixture followed by 5 g of anhydrous potassium carbonate. The mixture was stirred at room temperature for 24 hours and the mixture was precipitated into 400 ml water. The white solid product was washed three times with water and a further three times with methanol to yield 4.70 g (99.1% of theoretical yield) of a snow-white product which was further recrystallized from acetonitrile to yield 4.1 g of product with the formula: ##STR10## The melting point of this product was 247°-248° C. The elemental analysis for C30H26N4O2 was calc.: C, 75.94%; H, 5.48%; N, 11.81%; found: C, 76.07%; H, 5.51%; N, 1.86%.

Workup

  1. customfitted with a magnetic stirrer bar, nitrogen-gas inlet
  2. customthe mixture was precipitated into 400 ml water
  3. washThe white solid product was washed three times with water
  4. customa further three times with methanol to yield
  5. custom4.70 g (99.1% of theoretical yield) of a snow-white product which
  6. customwas further recrystallized from acetonitrile

Sources & evidence

ORD record
ord-2cb0419835394ffb85d8ca605891a9de
Source dataset
uspto-grants-1995_07
Patent number
US05434240

Reaction notes

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