Water → HCID 178494948, compound

Temperature

-5 °C

A suspension, gassed with nitrogen, of 11.4 g of (3-methoxypropyl)triphenylphosphonium iodide in 50 ml of tetra- hydrofuran is cooled to -5° C., treated with 3.36 g of potassium tert.-butylate, stirred at -5° C. for 10 minutes and at room temperature for 1 hour. After cooling the reaction mixture to -5° C. a solution of 4.6 g of [trans-4-(4-chlorophenyl)cyclo-hexyl]acetaldehyde in 25 ml of tetrahydrofuran is added dropwise within 5 minutes, the mixture is stirred at -5° C. for 10 minutes and at room temperature for 1 hour, treated with 50 ml of water and the aqueous phase is extracted with 100 ml of ethyl acetate. The organic phase is washed with water, dried over sodium sulphate, filtered and concentrated. The residue is taken up in 50 ml of toluene and dissolved by heating to 70° C. and stirring for 30 minutes. The solution is cooled to room temperature, treated with 50 ml of hexane, stirred for 2 hours, filtered and washed with 30 ml of toluene/hexane (1:1 vol.). The filtrate is filtered over 100 g of silica gel and the silica gel is washed with 200 ml of hexane/toluene (1:1 vol.). The filtrate; is concentrated and gives 5.4 g of 1-chloro-4-[trans-4-(5-methoxy-2-pentenyl)cyclo-hexyl]benzene. The following compounds can be manufactured in an analogous manner:

1. additionis added dropwise within 5 minutes
2. stirringthe mixture is stirred at -5° C. for 10 minutes and at room temperature for 1 hour
3. extractionthe aqueous phase is extracted with 100 ml of ethyl acetate
4. washThe organic phase is washed with water
5. dry with materialdried over sodium sulphate
6. filtrationfiltered
7. concentrationconcentrated
8. dissolutiondissolved
9. temperatureby heating to 70° C.
10. stirringstirring for 30 minutes
11. temperatureThe solution is cooled to room temperature
12. additiontreated with 50 ml of hexane
13. stirringstirred for 2 hours
14. filtrationfiltered
15. washwashed with 30 ml of toluene/hexane (1:1 vol.)
16. filtrationThe filtrate is filtered over 100 g of silica gel
17. washthe silica gel is washed with 200 ml of hexane/toluene (1:1 vol.)
18. concentrationis concentrated

ORD record

ord-0ea33665f34143659b64176a5740dd5d

Source dataset

uspto-grants-1995_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05399689