反应详情

温度

0 °C

A cooled (0° C.) solution of 4-methylthiophenol (Aldrich; 20.0 g; 161 mmol) in MeOH (400 ml) was treated with a 5 N solution of NaOH in water (40 mL) and with 1-iodopropane (18.0 ml; 185 mmol). The reaction was stirred at 0° C. for 1 h then concentrated under reduced pressure. The concentrated solution was diluted with EtOAc then washed with brine. The organic phase was dried on MgSO4, filtered and concentrated under reduced pressure to give a residue, which was dissolved in DCM (200 ml) and cooled to at 0° C. This solution was treated over 20 min with a suspension of 3-chloroperbenzoic acid (83.12 g; 337.2 mmol) in DCM (600 ml). The reaction suspension was stirred at 0° C. for 3 h then treated with a further portion of 3-chloroperbenzoic acid (18.86 g; 76.52 mmol) in DCM (150 ml). The reaction was warmed to RT and stirred for 16 h. The reaction solution was filtered and the filtrate reduced in volume under reduced pressure and diluted with EtOAc, then washed twice with a 1 N solution of NaOH in water and then brine. The organic phase was dried on MgSO4, filtered and concentrated under reduced pressure to give the title compound (24.80 g, 78%) as an oil which solidified upon standing.

1. concentrationthen concentrated under reduced pressure
2. additionThe concentrated solution was diluted with EtOAc
3. washthen washed with brine
4. customThe organic phase was dried on MgSO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customto give a residue, which
8. temperaturecooled to at 0° C
9. stirringThe reaction suspension was stirred at 0° C. for 3 h
10. temperatureThe reaction was warmed to RT
11. stirringstirred for 16 h
12. filtrationThe reaction solution was filtered
13. additiondiluted with EtOAc
14. washwashed twice with a 1 N solution of NaOH in water
15. customThe organic phase was dried on MgSO4
16. filtrationfiltered
17. concentrationconcentrated under reduced pressure