Ammonia → 3-Chloro-4-cyclohexylethynylbenzene

3-Chloro-4-cyclohexylacetophenone (0.25 moles) and phosphorus pentachloride (0.31 moles) are placed in a 3-necked flask equipped with a mechanical stirrer, a condenser connected to a nitrogen inlet, and a thermometer. The mixture is stirred at 33°-35° C for 3 days. The cooled reaction mixture is poured onto 800 g. of ice and extracted with 3 × 500 ml. of ether. The ether fraction is washed with 2 × 100 ml water 4 × 100 ml of 5% sodium hydroxide, 3 × 50 ml water, 2 × 50 ml of saturated saline and dried over sodium sulfate. The ether is removed to give the chlorinated intermediate. The intermediate is dissolved in anhydrous THF (200 ml) and is added dropwise to a freshly prepared solution of sodamide in liquid ammonia, using a dry-ice condenser. The reaction mixture is allowed to stir at room temperature overnight; then, it is poured into 50 ml of water and 500 ml of ether. The ether fraction is washed with 3 × 50 ml water and 50 ml of saturated saline and is dried over sodium sulfate. Removal of solvent gives a residue which is distilled to give 3-chloro-4-cyclohexylethynylbenzene.

1. customequipped with a mechanical stirrer, a condenser
2. customconnected to a nitrogen inlet
3. customThe cooled reaction mixture
4. additionis poured onto 800 g
5. extractionof ice and extracted with 3 × 500 ml
6. washThe ether fraction is washed with 2 × 100 ml water 4 × 100 ml of 5% sodium hydroxide, 3 × 50 ml water, 2 × 50 ml of saturated saline
7. dry with materialdried over sodium sulfate
8. customThe ether is removed
9. customto give the chlorinated intermediate
10. stirringto stir at room temperature overnight
11. washThe ether fraction is washed with 3 × 50 ml water and 50 ml of saturated saline
12. dry with materialis dried over sodium sulfate
13. customRemoval of solvent
14. customgives a residue which
15. distillationis distilled

ORD-Eintrag

ord-ecb805a6936d480fa5088b4766119712

Quelldatensatz

uspto-grants-1978_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04093737