Reacción #8582

Ecuación de reacción

2-Hydroxypropanol

triethylamine

dichloromethane

p-nitrobenzoyl chloride

→

title compound

Rendimiento 51.0%

2-Hydroxypropyl 4-nitrobenzoate

Rendimiento 51.0%

Disolventes

toluene

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat 0° C
2. 2
   workup.STIRRINGAfter stirring at the same temperature for 30 minutes
3. 3
   workup.ADDITIONwas slowly added
4. 4
   workup.STIRRINGstirred for 2 hours
5. 5
   Otrothe crystals thus precipitated
6. 6
   workup.DISSOLUTIONwere dissolved
7. 7
   LavadoThe solution was washed with an dilute aqueous solution of sodium hydrogencarbonate (100 ml)
8. 8
   OtroThe organic layer thus obtained
9. 9
   Concentraciónwas concentrated
10. 10
    workup.DISSOLUTIONthe residue was dissolved in toluene (45 ml)
11. 11
    Temperaturaby heating
12. 12
    TemperaturaThen it was cooled
13. 13
    Otroto stand at room temperature for crystallization
14. 14
    OtroThe crystals thus precipitated
15. 15
    Filtraciónwere collected by filtration
16. 16
    Otrodried under reduced pressure

Procedimiento

2-Hydroxypropanol (4.57 g) was dissolved in toluene (80 ml) by stirring and triethylamine (6.68 g) was dropped thereinto at 0° C. After stirring at the same temperature for 30 minutes, a solution of p-nitrobenzoyl chloride (11.4 g) dissolved in toluene (12 ml) was slowly added thereto. The resultant mixture was heated to room temperature and stirred for 2 hours. Next, dichloromethane (50 ml) was added and the crystals thus precipitated were dissolved. The solution was washed with an dilute aqueous solution of sodium hydrogencarbonate (100 ml) and then with an aqueous solution of hydrochloric acid (0.5 mol/l). The organic layer thus obtained was concentrated and the residue was dissolved in toluene (45 ml) by heating. Then it was cooled by allowed to stand at room temperature for crystallization. The crystals thus precipitated were collected by filtration and dried under reduced pressure to give 6.90 g (51%) of the title compound as yellow crystals.

Fuente