반응 #68700

반응 방정식

4-Nitrobenzoyl chloride

1-octadecanol

pyridine

→

octadecyl 4-nitrobenzoate

수율 52.2%

용매

dichloromethane

반응 조건

후처리

1. 1
   온도was heated to reflux
2. 2
   온도The reaction mixture was heated
3. 3
   온도to reflux for sixteen hours
4. 4
   세척The reaction mixture was washed with 250 milliliters of water
5. 5
   세척The aqueous layer was washed with 250 milliliters of dichloromethane
6. 6
   농축concentrated under reduced pressure to a light tan solid
7. 7
   workup.ADDITIONAdded 500 milliliters of hexane
8. 8
   온도heated to reflux
9. 9
   기타A white precipitate formed as the solution
10. 10
    온도was cooled to room temperature
11. 11
    여과Filtered off the white precipitate
12. 12
    농축concentrated the filtrate to a light tan solid
13. 13
    기타The solid was recrystallized from ethanol (500 milliliters)

실험 절차

Under a nitrogen atmosphere, a mixture of 1-octadecanol (36 grams, 210 mmol), pyridine (20 milliliters), and dichloromethane (500 milliliters) was heated to reflux. The alcohol dissolved and the solution was allowed to cool 5° C. 4-Nitrobenzoyl chloride (39.0 grams, 210 mmol) was added in portions over a twenty minute period. The reaction mixture was heated to reflux for sixteen hours. The reaction mixture was washed with 250 milliliters of water. The aqueous layer was washed with 250 milliliters of dichloromethane. The organic layers were combined and concentrated under reduced pressure to a light tan solid. Added 500 milliliters of hexane and heated to reflux. A white precipitate formed as the solution was cooled to room temperature. Filtered off the white precipitate and concentrated the filtrate to a light tan solid. The solid was recrystallized from ethanol (500 milliliters) to obtain 46 grams of octadecyl 4-nitrobenzoate as a white solid.

출처