Réaction #417932

Équation de réaction

HCl

3-phenylbutanoyl chloride

phenol

pyridine

→

colourless oil

Rendement 83.8%

Phenyl 3-phenylbutanoate

Rendement 83.8%

Solvants

toluene

toluene

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe mixture was stirred intensely for 15 min
2. 2
   Autretransferred into a separatory funnel
3. 3
   AutreThe aqueous layer was separated
4. 4
   Lavagethe organic layer washed 4 times with water
5. 5
   Séchagebrine and dried over MgSO4
6. 6
   AutreThe solvent was removed in a rotary evaporator
7. 7
   workup.DISTILLATIONthe residue short-path distilled at 125-128° C./0.07 mbar

Mode opératoire

To the solution of phenol (8.62 g, 92 mmol) and 4-dimethylaminopyridine (400 mg) in toluene (110 ml) was added pyridine (18.1 g, 229 mmol) and the resulting solution was cooled to 10° C. Then a solution of 3-phenylbutanoyl chloride (20.1 g, 110 mmol) was added dropwise. The resulting mixture was stirred at room temperature for 24 h, and then cooled to 5° C. before the careful addition of 2N aq. HCl-solution (225 ml). The mixture was stirred intensely for 15 min, then diluted with toluene and transferred into a separatory funnel. The aqueous layer was separated and the organic layer washed 4 times with water, then brine and dried over MgSO4. The solvent was removed in a rotary evaporator and the residue short-path distilled at 125-128° C./0.07 mbar to yield 18.52 g (70%) of colourless oil.

Source