Reaction #586079

Reaction equation

tetradecyl 4-nitrobenzoate

ethyl acetate

→

tetradecyl 4-aminobenzoate

Yield 65.2%

Solvents

Dichloromethane

Conditions

Workup

1. 1
   OtherUnder a nitrogen purge
2. 2
   Otherfor sixteen hours
3. 3
   Filtrationthe reaction mixture was filtered through a layer of CELITE
4. 4
   Filtrationfilter aid
5. 5
   ConcentrationThe filtrate was concentrated under reduced pressure to a tan solid
6. 6
   OtherThe solid was recrystallized from ethanol

Procedure

Under a nitrogen purge, 10% platinum on carbon (2.5 grams) was added to a mixture of tetradecyl 4-nitrobenzoate (25 grams, 69 mmol) and ethyl acetate (250 milliliters) in a Parr vessel. The vessel was placed under hydrogen pressure (49 psi, 3.3×105 Pa) for sixteen hours. Dichloromethane was added and the reaction mixture was filtered through a layer of CELITE filter aid. The filtrate was concentrated under reduced pressure to a tan solid. The solid was recrystallized from ethanol to obtain 15 grams of tetradecyl 4-aminobenzoate as light tan needles.

Source