تفاعل #8582

معادلة التفاعل

2-Hydroxypropanol

triethylamine

dichloromethane

p-nitrobenzoyl chloride

→

title compound

المردود 51.0%

2-Hydroxypropyl 4-nitrobenzoate

المردود 51.0%

المذيبات

toluene

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىat 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
   أخرىthe crystals thus precipitated
6. 6
   workup.DISSOLUTIONwere dissolved
7. 7
   غسيلThe solution was washed with an dilute aqueous solution of sodium hydrogencarbonate (100 ml)
8. 8
   أخرىThe organic layer thus obtained
9. 9
   تركيزwas concentrated
10. 10
    workup.DISSOLUTIONthe residue was dissolved in toluene (45 ml)
11. 11
    درجة الحرارةby heating
12. 12
    درجة الحرارةThen it was cooled
13. 13
    أخرىto stand at room temperature for crystallization
14. 14
    أخرىThe crystals thus precipitated
15. 15
    ترشيحwere collected by filtration
16. 16
    أخرىdried under reduced pressure

الإجراء التجريبي

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.

المصدر