Ammonia → HCID 20290315, compound

3-Cyclohexyl-cyclopentanone used hereinabove as starting material was prepared as indicated hereinafter: 16.6 g (0.148 Mole) of cyclohexyl chloride were added dropwise to 3.6 g (0.150 atome-g) of magnesium metal in a 250 ml vessel, under nitrogen atmosphere and in the presence of a iodine cristal. The reaction mixture was heated to reflux for 1 hour, then cooled to 0° and 1.42 g (0.074 Mole) of cuprous iodide were added thereto. After cooling the reaction mixture at -8°, 5.74 g (0.070 Mole) of cyclopent-2-ene-1-one in 40 ml of tetrahydrofurane were added dropwise. After having been stirred for 1 hour at -8°, the reaction mixture was poured onto 100 g of crushed ice, acidified with 15% HCl in water (pH 4-5) and finally neutralized by the addition of aqueous ammonia. After the addition of 10 g of NH4Cl the reaction mixture was extracted with ether (3×300 ml), washed with water (3×100 ml), dried over sodium sulfate and finally evaporated to afford 13.2 g of raw material. After purification by means of column chromatography (neutral Al2O3 --eluent:toluene) and subsequent distillation on a VIGREUX column, there were obtained 7.0 g (60% yield) of the desired product, b.p. 50°/0.005 Torr.

1. customwas prepared
2. temperatureThe reaction mixture was heated
3. temperatureto reflux for 1 hour
4. temperaturecooled to 0°
5. temperatureAfter cooling the reaction mixture at -8°
6. extractionwas extracted with ether (3×300 ml)
7. washwashed with water (3×100 ml)
8. dry with materialdried over sodium sulfate
9. customfinally evaporated
10. customto afford 13.2 g of raw material
11. customAfter purification
12. distillationby means of column chromatography (neutral Al2O3 --eluent:toluene) and subsequent distillation on a VIGREUX column

ORD record

ord-52b76aefbe504e29bea110c623960527

Source dataset

uspto-grants-1981_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04251398