Hydrochloric Acid → HCID 20470557, compound

Temperature

110 °C

Metallic magnesium (6.9 g, 0.28 mol) was introduced into a completely dried 1 l three-neck flask and the inside of the vessel was completely dried by passing dry nitrogen gas through it, followed by adding anhydrous tetrahydrofuran (50 ml) and a trace of iodine. An anhydrous tetrahydrofuran solution (146 ml) of 4-brom-1-(β-butyloxyethyl)-benzene (X1V) (73 g, 0.28 mol) was gradually added with stirring, while the temperature was maintained at 30°~35° C., followed by further reaction at the same temperature for 1.5 hour. The reaction liquid was ice-cooled to reduce the inner temperature down to 5° C. or lower, followed by adding an anhydrous tetrahydrofuran solution (146 ml) of 4-(p-bromophenyl)-cyclohexanone (X111) (72 g, 0.28 mol) obtained in Step G, at such a rate that the inner temperature did not exceed 10° C. After reaction at room temperature for 30 minutes, a small amount of 6 N--HCl was added to make the contents weakly acidic, followed by adding toluene (200 ml), separating the toluene layer from the aqueous layer, subjecting the aqueous layer to extraction with toluene (50 ml), combining the toluene layers together, washing the combined layers with water and removing toluene by concentration of the layers. To the resulting residue were added toluene (200 ml) and potassium hydrogen sulfate (10 g) and the mixture was heated and placed under reflux at 110° C. for one hour. After cooling, the toluene solution was washed with water to make it neutral, followed by removing toluene by concentration of the solution. The resulting raw crystals were recrystallized from ethanol (200 ml) to obtain 1-[p-(β-butyloxyethyl)-phenyl]-4-(p-bromophenyl)-cyclohexene (XV) (57.5 g) having a melting point of 86.5°~89.5° C.

1. customthe inside of the vessel was completely dried
2. additionby adding anhydrous tetrahydrofuran (50 ml)
3. temperaturewas maintained at 30°~35° C.
4. customfollowed by further reaction at the same temperature for 1.5 hour
5. customThe reaction liquid
6. temperaturecooled
7. customdown to 5° C.
8. customdid not exceed 10° C
9. customAfter reaction at room temperature for 30 minutes
10. customseparating the toluene layer from the aqueous layer
11. extractionto extraction with toluene (50 ml)
12. washwashing the combined layers with water
13. customremoving toluene by concentration of the layers
14. additionTo the resulting residue were added toluene (200 ml) and potassium hydrogen sulfate (10 g)
15. temperaturethe mixture was heated
16. temperatureAfter cooling
17. washthe toluene solution was washed with water
18. customby removing toluene by concentration of the solution
19. customThe resulting raw crystals were recrystallized from ethanol (200 ml)

ORD record

ord-2ace0d54742c44a4a08180d0da39ff87

Source dataset

uspto-grants-1984_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04431564