반응 #1108367

반응 방정식

H2SO4

Diamantane

CH2Cl2

HNO3

water

→

4.9-dihydroxydiamantane

수율 65.0%

용매

methanol

반응 조건

후처리

1. 1
   기타The CH2Cl2 is removed
2. 2
   온도the reaction mixture 26 is refluxed for 1.5 h
3. 3
   기타Removal of the water in the vacuum
4. 4
   기타yielded
5. 5
   workup.ADDITIONa mixture of different oligohydroxydes 20 as a remainder
6. 6
   workup.STIRRINGstirred for 2 h at room temperature
7. 7
   여과filtered
8. 8
   추출Extraction of the filtrate with one or several organic solvents (typically diethylether)

실험 절차

Diamantane 1 (1.28 g, 0.149 mol), CH2Cl2 (250 mL) and 100% HNO3 (90 mL, 2.13 mol) are mixed at 0° C., stirred for 2 h at 25° C. and subsequently diluted with water (180 mL). The CH2Cl2 is removed and the reaction mixture 26 is refluxed for 1.5 h. Removal of the water in the vacuum yielded a mixture of different oligohydroxydes 20 as a remainder. These 20 are added to 200 mL of 96% H2SO4 and stirred for 2 h at room temperature. Subsequently, the reaction mixture is poured onto 300 g ice and filtered. Extraction of the filtrate with one or several organic solvents (typically diethylether) yields 21.3 g (0.097 mmol, 65%) 4.9-dihydroxydiamantane (2, m=0) as white solid, mp. 291-293° C. (from methanol, literature 290-292° C.).

출처