Реакция #68700

Уравнение реакции

4-Nitrobenzoyl chloride

1-octadecanol

pyridine

→

octadecyl 4-nitrobenzoate

Выход 52.2%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   Температураwas heated to reflux
2. 2
   ТемператураThe reaction mixture was heated
3. 3
   Температураto reflux for sixteen hours
4. 4
   ПромывкаThe reaction mixture was washed with 250 milliliters of water
5. 5
   ПромывкаThe aqueous layer was washed with 250 milliliters of dichloromethane
6. 6
   Концентрированиеconcentrated under reduced pressure to a light tan solid
7. 7
   workup.ADDITIONAdded 500 milliliters of hexane
8. 8
   Температураheated to reflux
9. 9
   ДругоеA white precipitate formed as the solution
10. 10
    Температураwas cooled to room temperature
11. 11
    ФильтрацияFiltered off the white precipitate
12. 12
    Концентрированиеconcentrated the filtrate to a light tan solid
13. 13
    ДругоеThe solid was recrystallized from ethanol (500 milliliters)

Методика

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.

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