تفاعل #68700

معادلة التفاعل

4-Nitrobenzoyl chloride

1-octadecanol

pyridine

→

octadecyl 4-nitrobenzoate

المردود 52.2%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas heated to reflux
2. 2
   درجة الحرارةThe reaction mixture was heated
3. 3
   درجة الحرارةto reflux for sixteen hours
4. 4
   غسيلThe reaction mixture was washed with 250 milliliters of water
5. 5
   غسيلThe aqueous layer was washed with 250 milliliters of dichloromethane
6. 6
   تركيزconcentrated under reduced pressure to a light tan solid
7. 7
   workup.ADDITIONAdded 500 milliliters of hexane
8. 8
   درجة الحرارةheated to reflux
9. 9
   أخرىA white precipitate formed as the solution
10. 10
    درجة الحرارةwas cooled to room temperature
11. 11
    ترشيحFiltered off the white precipitate
12. 12
    تركيزconcentrated the filtrate to a light tan solid
13. 13
    أخرىThe solid was recrystallized from ethanol (500 milliliters)

الإجراء التجريبي

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.

المصدر