Ammonium Chloride → HCID 22908546, Verbindung

Temperatur

60 °C

A mixture of dry Mg (0.77 g, 0.032 mol), 2-(4-trifluoromethylphenyl)ethyl bromide (8.0 g, 0.032 mol) obtained at the second step and diethyl ether (40 ml) was heated at 60° C. for one hour in a sealed tube reactor to obtain a gray, uniform solution, followed by adding this solution to a diethyl ether (30 ml) solution of 4-(4-pentylcyclohexyl)cyclohexanone (7.9 g, 0.032 mol), stirring the mixture at room temperature for 3 hours, feeding the resulting reaction substance into a saturated aqueous solution of NH4Cl, twice extracting with ethyl acetate (50 ml), washing the resulting organic layer, with an aqueous solution of NaCl, drying over anhydrous MgSO4, removing anhydrous MgSO4, distilling off the solvent under reduced pressure, to obtain pale yellow, oily 1-(2-(4-trifluoromethylphenyl)ethyl)-4-(4-pentylcyclohexyl)cyclohexanol (11.4 g), adding thereto toluene (50 ml) and Amberlyst (0.7 g), heating the mixture under reflux for one hour, while removing water formed by the reaction, allowing the resulting substance to cool, feeding it to a saturated aqueous solution of NH4Cl (100 ml), twice washing the resulting separated organic layer with water, drying over anhydrous magnesium sulfate, filtering off the anhydrous MgSO4, distilling off the solvent under reduced pressure, subjecting the resulting residue to column chromatography (silica gel, eluent: heptane) and twice recrystallizing from ethanol (20 ml), to obtain 1-(2 -(4-trifluoromethylphenyl)ethyl)-4-(4-pentylcyclohexyl)cyclohexene (4.1 g). Yield: 32%.

1. customto obtain a gray, uniform solution
2. extractiontwice extracting with ethyl acetate (50 ml)
3. washwashing the resulting organic layer
4. dry with materialwith an aqueous solution of NaCl, drying over anhydrous MgSO4
5. customremoving anhydrous MgSO4
6. distillationdistilling off the solvent under reduced pressure
7. customto obtain pale yellow
8. temperatureunder reflux for one hour
9. customwhile removing water
10. customformed by the reaction
11. temperatureto cool
12. washtwice washing the resulting
13. customseparated organic layer with water
14. dry with materialdrying over anhydrous magnesium sulfate
15. filtrationfiltering off the anhydrous MgSO4
16. distillationdistilling off the solvent under reduced pressure
17. customtwice recrystallizing from ethanol (20 ml)

ORD-Eintrag

ord-3b4f1934a2ed45d393c4b892c1192b99

Quelldatensatz

uspto-grants-1996_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05534187