Sulfuric Acid → (-)-cis-1,2-Dimethoxy-4-(2-aminocyclohexyl)benzene
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:14][CH:13]=[CH:12][CH2:11][C@@H:10]2[N+:15]([O-])=O)=[CH:5][C:4]=1[O:18][CH3:19].COC1C=CC([C@@H]2CC=CC[C@H]2[N+]([O-])=O)=CC=1OC.[OH-].[K+].S(=O)(=O)(O)O>C(O)C.CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[NH2:15])=[CH:5][C:4]=1[O:18][CH3:19]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Specific rotation: [ α ] D 20 = - 58.5 ° C ( c = 1 , ethanol ) . C1. (+/−)-cis-1,2-Dimethoxy-4-(2-nitrocyclohex-4-enyl)benzene 10.0 g of (+/−)-trans-1,2-dimethoxy-4-(2-nitrocyclohex-4-enyl)benzene and 20.0 g of potassium hydroxide are dissolved in 150 ml of ethanol and 35 ml of dimethylformamide. A solution of 17.5 ml of conc. sulfuric acid in 60 ml of ethanol is then added dropwise such that the internal temperature does not exceed 4° C. After stirring for 1 h, the mixture is added to 1 l of ice water, the precipitate is filtered off with suction, washed with water and dried, and the crude product is recrystallized from ethanol. 8.6 g of the title compound of m. p. 82.5-84° C. are obtained. C2. (+/−)-cis-1,2-Dimethoxy-4-(2-nitrocyclohexyl)benzene
Workup
- custom[ α ] D 20 = - 58.5 °
- customdoes not exceed 4° C
- filtrationthe precipitate is filtered off with suction
- washwashed with water
- customdried
- customthe crude product is recrystallized from ethanol
Sources & evidence
- ORD record
- ord-6e680ba8a44c45ffba6f1309724e2aea
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06884802B2
Reaction notes
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