Reaction #586078

Reaction equation

1-tetradecanol

pyridine

4-Nitrobenzoyl chloride

→

tetradecyl 4-nitrobenzoate

Solvents

dichloromethane

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was heated
2. 2
   Temperatureto reflux for sixteen hours
3. 3
   WashThe reaction mixture was then washed twice with water (2×500 milliliters)
4. 4
   ConcentrationThe organic layer was concentrated under reduced pressure to a yellow solid
5. 5
   workup.ADDITIONOne thousand (1000) milliliters of hexane was added
6. 6
   Temperaturethe mixture was heated to reflux
7. 7
   TemperatureThe mixture was cooled
8. 8
   Concentrationconcentrated
9. 9
   Otherto yield a yellow solid
10. 10
    Filtrationthat was filtered
11. 11
    OtherThe yellow solid was recrystallized twice from ethanol

Procedure

Under a nitrogen atmosphere, a mixture of 1-tetradecanol (96.3 grams, 449 millimoles (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 then washed twice with water (2×500 milliliters). The organic layer was concentrated under reduced pressure to a yellow solid. One thousand (1000) milliliters of hexane was added, and the mixture was heated to reflux. The mixture was cooled and concentrated to yield a yellow solid that was filtered. The yellow solid was recrystallized twice from ethanol to obtain 77.0 grams of tetradecyl 4-nitrobenzoate as yellow crystals.

Source