Potassium Carbonate → 1,2-Dicyano-2-(tert-butylcyclohexyloxy)benzene
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
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, followedby 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
- customAfter the completion of the reaction
- 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
- extractionextracted with ethyl acetate
- dry with materialwas dried overnight with the use of MgSO4, followedby removal of ethyl acetate by distillation
- customThe residues were isolated
- custompurified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-1282bcb89d0f4aedbd5b4eb31b9cc18e
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05569504
Reaction notes
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