Methanol → HCID 178442528, compound

Temperature

110 °C

4-(4'-Heptylphenyl)phenol (200 g) was dissolved in ethanol (0.5 l) and a commercially available Raney nickel catalyst (20 g) was added, followed by hydrogenation at 80°~120° C. under hydrogen pressures of 30~40 Kg/cm2G for 6 hours in an autoclave. The reaction was traced by gas chromatography (column: SIDC-560-10%, 2 m, 280° C.), and when the raw material was extinct, the reaction was stopped. The catalyst was filtered off from the hydrogenation product, and after ethanol was distilled off under reduced pressure, the product was dissolved in toluene (200 ml). On the other hand, metallic sodium (18.4 g) was added to toluene (400 ml), followed by heating to 110° C. and then quenching down to room temperature under high speed agitation to prepare a sodium dispersion. To this dispersion was added the above toluene solution of the hydrogenation product, followed by stirring at room temperature for one hour. The mixture was further agitated at 100° C. for 4 hours, followed by cooling and then gradually adding methanol (200 ml). The whole mixture was transferred into a separating funnel and washed twice with 10% hydrochloric acid (200 ml) and once with a saturated aqueous solution of sodium hydrogen carbonate (200 ml), followed by repeated washings with water until the water layer became neutral. The toluene layer was dried over anhydrous sodium sulfate and toluene was distilled off under reduced pressure, followed by adding n-hexane (200 ml) and standing still overnight obtain crystals of trans-4-(4'-heptylphenyl)cyclohexanol. Yield: 41.6 g, 20.4%, m.p.: 80.2°~82.5° C.

1. customfollowed by hydrogenation at 80°~120° C. under hydrogen
2. customfor 6 hours
3. customwas traced by gas chromatography (column: SIDC-560-10%, 2 m, 280° C.), and when
4. filtrationThe catalyst was filtered off from the hydrogenation product
5. distillationafter ethanol was distilled off under reduced pressure
6. dissolutionthe product was dissolved in toluene (200 ml)
7. additionOn the other hand, metallic sodium (18.4 g) was added to toluene (400 ml)
8. customquenching down to room temperature under high speed agitation
9. customto prepare a sodium dispersion
10. stirringThe mixture was further agitated at 100° C. for 4 hours
11. temperatureby cooling
12. customThe whole mixture was transferred into a separating funnel
13. washwashed twice with 10% hydrochloric acid (200 ml) and once with a saturated aqueous solution of sodium hydrogen carbonate (200 ml)
14. washwashings with water until the water layer
15. dry with materialThe toluene layer was dried over anhydrous sodium sulfate and toluene
16. distillationwas distilled off under reduced pressure
17. additionby adding n-hexane (200 ml)
18. waitstanding still overnight

ORD record

ord-e844aa0870014f6d8ca3171ce9e0edfb

Source dataset

uspto-grants-1983_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04405488