Toluene → (S)-1-(4'-octyloxy-4-biphenylyloxy)-propan-2-ol

Temperature

60 °C

A solution of (2S)-2-(2'-tetrahydropyranyloxy)-1-(p-toluenesulfonyloxy)-propane (20 g) in N,N-dimethylformamide (hereinafter abbreviated to DMF) (300 ml) was added to a mixture of sodium hydride (60%) (2 g), 4-hydroxy-4'-octyloxy-biphenyl(10 g) and tetrahydrofuran (hereinafter abbreviated to THF) (200 ml), followed by agitating the resulting mixture at 60° C. for 4 hours, allowing it to cool down to room temperature, adding toluene (300 ml) and water (300 ml), separating the resulting organic layer, washing it with an alkali solution and then with water, concentrating it, adding ethanol (300 ml) and pyridium p-toluenesulfonate (hereinafter abbreviated to PPTS) (2 g), agitating the mixture at 50° C. for 3 hours, distilling off ethanol, adding toluene (300 ml), washing the resulting organic layer with water, concentrating it and recrystallizing the concentrate, to obtain (S)-1-(4'-octyloxy-4-biphenylyloxy)-propan-2-ol (8 g).

1. temperatureto cool down to room temperature
2. customseparating the resulting organic layer
3. washwashing it with an alkali solution
4. concentrationwith water, concentrating it
5. additionadding ethanol (300 ml) and pyridium p-toluenesulfonate (hereinafter abbreviated to PPTS) (2 g)
6. stirringagitating the mixture at 50° C. for 3 hours
7. distillationdistilling off ethanol
8. additionadding toluene (300 ml)
9. washwashing the resulting organic layer with water
10. concentrationconcentrating it
11. customrecrystallizing the concentrate

ORD record

ord-234402a025d241d5ade7f332faa3b8dc

Source dataset

uspto-grants-1990_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04973426