反应详情

温度

5 °C

The compound (III) (50 g, 0.268 mol) obtained in the first step was dissolved in dry pyridine (110 ml) and the solution was cooled to 5° C. or lower. To this solution was dropwise added a solution of p-toluenesulfonic acid chloride (50.1 g, 0.263 mol) dissolved in dry toluene (70 ml), in small portions through a dropping funnel so that the reaction temperature did not exceed 10° C. After completion of the dropwise addition, the cooling bath was removed and the reaction mixture was agitated at room temperature for 4 hours, followed by adding water (100 ml) and toluene (300 ml) and stirring. The mixture was transferred into a separating funnel and the toluene layer was washed twice with 6N-HCl aqueous solution (100 ml), then once with water (200 ml), further twice with 2N-NaOH aqueous solution (100 ml) and then four times with water (200 ml). Toluene was distilled off under reduced pressure and the resulting crystals were recrystallized from toluene (90 ml), followed by separating the crystals by filtration to obtain p-toluenesulfonic acid (trans-4-phenylcyclohexylmethyl) ester (IV) (77 g) having a melting point of 108.0°~108.7° C.

1. customdid not exceed 10° C
2. additionAfter completion of the dropwise addition
3. customthe cooling bath was removed
4. additionby adding water (100 ml) and toluene (300 ml)
5. stirringstirring
6. customThe mixture was transferred into a separating funnel
7. washthe toluene layer was washed twice with 6N-HCl aqueous solution (100 ml)
8. distillationToluene was distilled off under reduced pressure
9. customthe resulting crystals were recrystallized from toluene (90 ml)
10. customby separating the crystals
11. filtrationby filtration