Reaktion #68698

Reaktionsgleichung

1-tetradecanol

pyridine

4-Nitrobenzoyl chloride

→

tetradecyl 4-nitrobenzoate

Ausbeute 47.2%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was heated
2. 2
   Temperaturto reflux for sixteen hours
3. 3
   WaschenThe reaction mixture was washed with water (2×500 milliliters)
4. 4
   EinengenThe organic layer was concentrated under reduced pressure to a yellow solid
5. 5
   workup.ADDITION1000 milliliters of hexane was added
6. 6
   Temperaturthe mixture was heated to reflux
7. 7
   TemperaturThe mixture was cooled
8. 8
   Filtrationfiltered
9. 9
   EinengenThe filtrate was concentrated
10. 10
    Sonstigeto yield a yellow solid
11. 11
    SonstigeThe yellow solid was recrystallized twice from ethanol

Vorschrift

Under a nitrogen atmosphere, a mixture of 1-tetradecanol (96.3 grams, 449 mmol), pyridine (40 milliliters), and dichloromethane (1000 milliliters) was heated to 30° C. 4-Nitrobenzoyl chloride (100 grams, 539 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 water (2×500 milliliters). The organic layer was concentrated under reduced pressure to a yellow solid. 1000 milliliters of hexane was added and the mixture was heated to reflux. The mixture was cooled and filtered. The filtrate was concentrated to yield a yellow solid. The yellow solid was recrystallized twice from ethanol to obtain 77.0 grams of tetradecyl 4-nitrobenzoate as yellow crystals.

Quelle