P-Cresol → N,N-diisopropyl-3-phenyl-3-(2-hydroxy-5-methylphenyl)propionamide

반응식

[CH:1]([N:4]([CH:16]([CH3:18])[CH3:17])[C:5](=[O:15])[CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)O)([CH3:3])[CH3:2].[CH:19]1[C:24]([OH:25])=[CH:23][CH:22]=[C:21]([CH3:26])[CH:20]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[OH:25][C:24]1[CH:23]=[CH:22][C:21]([CH3:26])=[CH:20][C:19]=1[CH:7]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:6][C:5]([N:4]([CH:16]([CH3:18])[CH3:17])[CH:1]([CH3:2])[CH3:3])=[O:15]

참가 물질

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.