Toluene → 2-Isopentylcyclopent-2-en-1-one

반응식

C(O[C:5](=[O:7])[CH3:6])(=O)C.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11](S(O)(=O)=O)=[CH:10][CH:9]=1.[C:19]1(C)C=CC=CC=1>>[CH3:19][CH:8]([CH3:18])[CH2:13][CH2:12][C:11]1[C:5](=[O:7])[CH2:6][CH2:9][CH:10]=1

참가 물질

반응물 3

HCID 1140Toluene

HCID 6101p-Toluenesulfonic acid

HCID 7918Acetic Anhydride

생성물 1

HCID 1224642-Isopentylcyclopent-2-en-1-one

반응 조건

온도: 125 °C

실험 절차

2-(3-Methyl-butyllidene)-cyclopentanone (1.093 Kg, 7.19 mol, obtained as detailed above), acetic anhydride (300 mL, 3.17 mol), p-toluenesulfonic acid (PTSA, 10 g), and toluene (500 mL) were charged into a flask and heated to 120-130° C. When gas chromatography analysis indicated the completion of the reaction, the reaction mixture was cooled to room temperature and quenched with Na2CO3 solution (100 mL). The resulting mixture was washed twice with brine (1 L). A rushover process provided the crude product 2-(3-methyl-butyl)-cyclopent-2-enone.