Acetic Acid → (-)-cis-1,2-Dimethoxy-4-(2-aminocyclohexyl)benzene

HRID 986951Notes

Reaction equation

HRID 986951 reaction equation
[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[N+:15]([O-])=O)=[CH:5][C:4]=1[O:18][CH3:19].C(O)(=O)C>C(O)C.[Zn]>[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

5

Reactant 2

HCID 176Acetic AcidHCID 15389590(+/-)-cis1,2-Dimethoxy-4-(2-nitrocyclohexyl)benzene

Product 1

HCID 14321190(-)-cis-1,2-Dimethoxy-4-(2-aminocyclohexyl)benzeneYield 88.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

125 g of (+/−)-cis-1,2-dimethoxy-4-(2-nitrocyclohexyl)benzene and 120 g of zinc powder or granules are suspended in 1300 ml of ethanol. 220 ml of acetic acid are added dropwise at boiling heat. The precipitate is filtered off with suction and washed with ethanol, and the filtrate is concentrated under reduced pressure. The residue is taken up in hydrochloric acid and extracted with toluene. The aqueous phase is rendered alkaline using 50% strength sodium hydroxide solution, the precipitate is filtered off with suction and the filtrate is extracted with toluene. The organic phase is dried using sodium sulfate and concentrated. 98 g of the title compound are obtained as a crystallizing oil.

Workup

  1. temperatureat boiling heat
  2. filtrationThe precipitate is filtered off with suction
  3. washwashed with ethanol
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. extractionextracted with toluene
  6. filtrationthe precipitate is filtered off with suction
  7. extractionthe filtrate is extracted with toluene
  8. customThe organic phase is dried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e98f641cd04f420ba9d0a504b52f791d
Source dataset
uspto-grants-2003_10
Patent number
US06630483B2

Reaction notes

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