Reaktion #58352

Reaktionsgleichung

(±)-cis-1,2-dimethoxy-4-(2-nitrocyclohex-4-enyl)benzene

acetic acid

→

title compound

Ausbeute 32.4%

(±)-cis-6-(3,4-Dimethoxyphenyl)-cyclohex-3-enylamine

Ausbeute 32.4%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter heating
2. 2
   workup.ADDITIONare added dropwise
3. 3
   FiltrationAfterwards, the reaction mixture is filtrated
4. 4
   Einengenconcentrated
5. 5
   workup.DISSOLUTIONThe residue is redissolved in diluted hydrochloric acid and extraxted with toluene
6. 6
   Extraktionextracted several times with toluene
7. 7
   ExtraktionThe combined organic phases of the alkalic extraction
8. 8
   Sonstigeare dried
9. 9
   Einengenconcentrated
10. 10
    SonstigeThe residue is chromatographed on silica gel using
11. 11
    workup.ADDITIONa mixture of petroleum ether/ethyl acetate/triethylamine in the ratio 6/3/1

Vorschrift

40 g of (±)-cis-1,2-dimethoxy-4-(2-nitrocyclohex-4-enyl)benzene (compound H1) are dissolved in 400 ml of ethanol and 40 g of zinc powder are added. After heating to boiling temperature, 65 ml of glacial acetic acid are added dropwise. Afterwards, the reaction mixture is filtrated and concentrated. The residue is redissolved in diluted hydrochloric acid and extraxted with toluene. The aqueous layer is alkalized using 6 N solution of sodium hydroxide and extracted several times with toluene. The combined organic phases of the alkalic extraction are dried using sodium sulfate and concentrated. The residue is chromatographed on silica gel using a mixture of petroleum ether/ethyl acetate/triethylamine in the ratio 6/3/1. 11.5 g of the title compound are obtained.

Quelle