Reaktion #8582

Reaktionsgleichung

2-Hydroxypropanol

triethylamine

dichloromethane

p-nitrobenzoyl chloride

→

title compound

Ausbeute 51.0%

2-Hydroxypropyl 4-nitrobenzoate

Ausbeute 51.0%

Lösungsmittel

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat 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
   Sonstigethe crystals thus precipitated
6. 6
   workup.DISSOLUTIONwere dissolved
7. 7
   WaschenThe solution was washed with an dilute aqueous solution of sodium hydrogencarbonate (100 ml)
8. 8
   SonstigeThe organic layer thus obtained
9. 9
   Einengenwas concentrated
10. 10
    workup.DISSOLUTIONthe residue was dissolved in toluene (45 ml)
11. 11
    Temperaturby heating
12. 12
    TemperaturThen it was cooled
13. 13
    Sonstigeto stand at room temperature for crystallization
14. 14
    SonstigeThe crystals thus precipitated
15. 15
    Filtrationwere collected by filtration
16. 16
    Sonstigedried under reduced pressure

Vorschrift

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.

Quelle