초록
니트로 알코올은 브로모 알코올의 치환반응으로 얻었다. 두번째 니트로 원자단은 사슬 길이에 따라 다른 방법으로 도입했다. 3,3-dinitro-1-propanol은 분자내 염기성 니트로화 반응으로 형성되면 5,5-dinitro-1-pentanol은 산화촉매 니트로화 반응으로 얻었다. 3,3-dinitro-1,6-hexanediol과 4,4-dinitro-1,8-octanediol은 3,3-dinitro-1-propanol과 5,5-dinitro-1-pentanol에 acrolein을 가해 Michael 반응으로 알데히드를 얻고 환원하여 합성했다. 치환반응시 알코올 보호기는 아세틸기가 좋으며 산화촉매 니트로 반응에서는 THP 원자단이 좋은 보호기이다.
Nitroalcohols were prepared by a substitution reaction from the corresponding bromoalcohols. The second nitro group was introduced via different methods depending on the carbon chain length. 3,3-Dinitro-1-propanol was obtained by an intramolecular varient of the alkaline nitration method. Whereas 5,5-dinitro-1-pentanol was given by the catalytic oxidative nitration. 3,3-Dinitro-1-propanol and 5,5-dinitro-1-pentanol were converted to 3,3-dinitro-1,6-hexanediol and 4,4-dinitro-1,8-octanediol via Michael reaction with acrolein followed by the reduction of the resulting aldehydes. Acetyl group was a good protecting group for the substitution reaction while THP was for the catalytic oxidative nitration.
