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o-Hydroxybenzophenones와 Phenylacetic Acid, Acetic Anhydride에 의한 Coumarin 유도체 합성에 관한 연구

Synthetic Studies of Coumarin Derivatives from o-Hydroxybenzophenones with Phenylacetic Acid and Acetic Anhydride

대한화학회지 1999년 43권 1호 p.92 ~ 103
강순희, 양성윤,
소속 상세정보
강순희 ( Kang Soon-Hee ) - Ewha Womans University College of Education Department of Science Education
양성윤 ( Yang Sung-Yun ) - Ewha Womans University College of Education Department of Science Education

Abstract

o-Hydroxybenzophenone 유도체 (2-hydroxybenzophenone, 2,2'-dihydroxybenzo phenone, 2,4-dihydroxybenzophenone, 2-hydroxy-5-methylbenzophenone, 5-chloro-2-hydroxy-4-methylbenzophenone 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-ethoxybenzophenone, 2-hydroxy-4,4'-dimethoxybenzophenone)들을 출발물질로 하여 8종의 coumarin 유도체들을 합성하였다. o-Hydroxybenzophenone과 같은 몰량의 phenylacetic acid를 사용하여 염기인 triethylamine(TEA)와 acetic anhydride를 o-hydroxybenzophenone에 대해 1:8의 비율로 아세톤에서 환류온도로 반응시켜 coumarin 유도체들을 합성한 경우가 가장 수득율이 좋았다. 이것은 용매로 acetic anhydride를 사용한 Sham와 Ray 방법보다 좋은 결과였다.

The 8 coumarin derivatives have been synthesized from 8 starting materials(2-hydroxy-benzophenone, 2,2'-dihydroxybenzophenone, 2,4-dihydroxybenzophenone, 2-hydroxy-5-methylbenzophenone, 5-chloro-2-hydroxy-4-methylbenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-ethoxybenzophenone, 2-hydroxy-4,4'-dimethoxybenzophenone) with phenylacetic acid and Ac2O/TEA in acetone at reflux temperature. The ratio of o-hydroxybenzophenone, phenylacetic acid, Ac2O and TEA is 1 : 1: 8: 8 in acetone. Our results showed higher products yields of coumarin derivatives than Shama and Ray's method in previous papers. A new intermediate form was proposed to our mechanism of coumarin synthetic method.

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