反応 #8582

反応方程式

2-Hydroxypropanol

triethylamine

dichloromethane

p-nitrobenzoyl chloride

→

title compound

収率 51.0%

2-Hydroxypropyl 4-nitrobenzoate

収率 51.0%

溶媒

toluene

toluene

反応条件

後処理

1. 1
   その他at 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
   その他the crystals thus precipitated
6. 6
   workup.DISSOLUTIONwere dissolved
7. 7
   洗浄The solution was washed with an dilute aqueous solution of sodium hydrogencarbonate (100 ml)
8. 8
   その他The organic layer thus obtained
9. 9
   濃縮was concentrated
10. 10
    workup.DISSOLUTIONthe residue was dissolved in toluene (45 ml)
11. 11
    温度by heating
12. 12
    温度Then it was cooled
13. 13
    その他to stand at room temperature for crystallization
14. 14
    その他The crystals thus precipitated
15. 15
    ろ過were collected by filtration
16. 16
    その他dried under reduced pressure

実験手順

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.

出典