Réaction #57507

Équation de réaction

NaOH

N,N-diisopropyl-3-phenyl-3-hydroxy-propionamide

p-cresol

→

product

Rendement 34.5%

3-(2-hydroxy-5-methyl-phenyl)-N,N-diisopropyl-3-phenyl-propionamide

Rendement 34.5%

Solvants

toluene

—

ice water

Conditions de réaction

Traitement

1. 1
   AutreA three-necked round-bottom flask equipped with condenser, mechanical stirrer
2. 2
   workup.WAITleft
3. 3
   workup.STIRRINGunder stirring for 30 minutes
4. 4
   AutreThe phases are separated
5. 5
   Extractionthe aqueous phase is extracted with toluene (2×30 ml)
6. 6
   SéchageThe combined organic phases are dried over sodium sulfate
7. 7
   Autreevaporated to dryness
8. 8
   AutreThe resulting oil is purified by flash chromatography (hexane/ethyl acetate 7:3)

Mode opératoire

A three-necked round-bottom flask equipped with condenser, mechanical stirrer, thermometer, is loaded with N,N-diisopropyl-3-phenyl-3-hydroxy-propionamide (1.0 g; 0.0041 mol), p-cresol (0.48 g; 0.0044 mol) and polyphosphoric acid (16.5 g). After five hours under stirring at room temperature the reaction is completed. The reaction mixture is poured in ice/water (10 g), alkalinized to pH 9-10 with NaOH 50% w/w and left under stirring for 30 minutes, then diluted with toluene (30 ml). The phases are separated and the aqueous phase is extracted with toluene (2×30 ml). The combined organic phases are dried over sodium sulfate and evaporated to dryness. The resulting oil is purified by flash chromatography (hexane/ethyl acetate 7:3). 0.48 g of product, as a pale yellow oil, are obtained.

Source