반응 #57507

반응 방정식

NaOH

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

p-cresol

→

product

수율 34.5%

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

수율 34.5%

용매

toluene

—

ice water

반응 조건

후처리

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

실험 절차

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.

출처