Potassium Carbonate → 1,2-Dicyano-2-(tert-butylcyclohexyloxy)benzene

HRID 850243Notes

Reaction equation

HRID 850243 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].[C:14]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1O)([CH3:17])([CH3:16])[CH3:15].C([O-])([O-])=[O:26].[K+].[K+]>CN(C)C=O>[C:1]([CH:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1([C:12]#[N:13])[O:26][C:18]1([C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 260682-tert-ButylcyclohexanolHCID 1626521,2-Benzenedicarbonitrile, 3-nitro-

Product 1

HCID 193624701,2-Dicyano-2-(tert-butylcyclohexyloxy)benzeneYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,2-dicyano-3-nitrobenzene (1.73 g) and 2-tert-butyl-cyclohexanol (4.68 g) were allowed to react with each other at 80° C. for 2 hours in dimethylformamide (DMF, 5 ml) with the addition of K2CO3 (5.0 g). After the completion of the reaction, the reaction product was extracted twice with a mixed solvent of water and ethyl acetate (at a volumetric ratio of 1/1), and the layer extracted with ethyl acetate was dried overnight with the use of MgSO4, followed by removal of ethyl acetate by distillation. The residues were isolated and purified by silica gel column chromatography using chloroform to obtain 1.41 g of 1,2-dicyano-2-(tert-butylcyclohexyloxy)benzene in a 50% yield.

Workup

  1. customAfter the completion of the reaction
  2. extractionthe reaction product was extracted twice with a mixed solvent of water and ethyl acetate (at a volumetric ratio of 1/1), and the layer
  3. extractionextracted with ethyl acetate
  4. dry with materialwas dried overnight with the use of MgSO4
  5. customfollowed by removal of ethyl acetate by distillation
  6. customThe residues were isolated
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-0e7211e0fc1e4edfa0f004c7e6efb7fd
Source dataset
uspto-grants-2000_01
Patent number
US06017604

Reaction notes

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