Sulfuric Acid → (+/-)-cis-1 2-Dimethoxy-4-(2-nitrocyclohex-4-enyl)benzene

HRID 30075

Reaction equation

HRID 30075 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-:17])=[O:16])=[CH:5][C:4]=1[O:18][CH3:19].[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][CH:13]=[CH:12][CH2:11][C@@H:10]2[N+:15]([O-:17])=[O:16])=[CH:5][C:4]=1[O:18][CH3:19]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 53874256(+/-)-trans-1,2-DI methoxy-4-(2-nitrocyclohex-4-enyl)benzene

Product 1

HCID 15389588(+/-)-cis-1 2-Dimethoxy-4-(2-nitrocyclohex-4-enyl)benzeneYield 86%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

10.0 g of (±)-trans-1,2-dimethoxy-4-(2-nitrocyclohex-4-enyl)benzene (compound I1) 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 in ethanol. 8.6 g of the title compound of m.p. 82.5-84° C. are obtained.

Workup

  1. customdoes not exceed 4° C
  2. filtrationthe precipitate is filtered off with suction
  3. washwashed with water
  4. customdried
  5. customthe crude product is recrystallized in ethanol

Sources & evidence

ORD record
ord-1992588b47a64cf89c55eec6b9345a4d
Source dataset
uspto-grants-2008_09
Patent number
US07423046B2

Linked notes

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