Réaction #89801

Équation de réaction

2-pyrrolidinone

ethyl acetate

potash

2-pyrrolidinone

bromododecane

→

N-dodecylpyrrolidin-2-one

Rendement 80.0%

Solvants

water

cyclohexane

toluene

Conditions de réaction

Traitement

1. 1
   Températurecooling
2. 2
   AutreThe aqueous and organic phases are separated
3. 3
   Extractionthe aqueous phase is extracted once with diethylether (60 mL)
4. 4
   Séchagedried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   workup.DISTILLATIONAfter vacuum distillation (146° C.-0.5 mbars)

Mode opératoire

Step A is conducted by adding tetrabutylammonium bromide (950 mg-3 mmol-0.05 eq.) and powder potash (23.1 g-411 mmol-7 eq.) under agitation to a solution of 2-pyrrolidinone (5.00 g-58.8 mmol) and bromododecane (18.5 mL, 76.4 mmol, 1.3 eq.) in toluene (60 mL). The mixture is heated to 50° C. overnight. After disappearance of the 2-pyrrolidinone (verified by TLC using a 4:1 v/v mixture of ethyl acetate and cyclohexane, and phosphomolybdic acid for detection) and cooling, 60 mL of water is added and the mixture left under agitation for a further 15 minutes. The aqueous and organic phases are separated and the aqueous phase is extracted once with diethylether (60 mL). The organic phases are combined, dried over Na2SO4, filtered and concentrated. After vacuum distillation (146° C.-0.5 mbars), N-dodecylpyrrolidin-2-one is obtained (Yield: 80%) for which the 1H and 13C NMR characterisations are as follows:

Source