Réaction #64670

Équation de réaction

DCC

1,16-hexadecanedioic acid

N-hydroxyphthalimide

→

N-(15-carboxypentadecanoyloxy)phthalimide

Rendement 41.1%

Solvants

tetrahydrofuran

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe resulting mixture was stirred overnight
2. 2
   FiltrationThe reaction mixture was filtered
3. 3
   Concentrationthe filtrate was concentrated under reduced pressure
4. 4
   AutreThe residue was separated
5. 5
   Autrepurified by silica gel chromatography

Mode opératoire

In 15 ml of anhydrous tetrahydrufuran 1,16-hexadecanedioic acid (500 mg, 1.75 mmoles) was dissolved. To the obtained solution, were added a solution of N-hydroxyphthalimide (285 mg, 1.75 mmoles) in 10 ml of anhydrous tetrahydrofuran and N,N-dimethylaminopyridine hydrochloride (1.4 mg) and the mixture was stirred for 30 minutes. To the mixture was added a solution of DCC (361 mg, 1.75 mmoles) in 3 ml of anhydrous tetrahydrofuran and the resulting mixture was stirred overnight. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was separated and purified by silica gel chromatography, to give N-(15-carboxypentadecanoyloxy)phthalimide (310 mg, 41%) having the following properties.

Source