53293-05-3Relevant articles and documents
An Unambiguous Synthesis of Melannein
Ahluwalia, V. K.,Kapur, Kanchan,Manchanda, Saroj
, p. 186 - 188 (2007/10/02)
Melannein (6-hydroxy-7-methoxy-4-(3'-hydroxy-4'-methoxyphenyl)coumarin, I) and its O,O-diethyl ether (II) have been synthesised.The steps involved in the synthesis of I and II are the respective condensation of o-methoxyhydroquinone with ethyl m-benzyloxy-p-methoxybenzoylacetate (XI) and ethyl m-ethoxy-p-methoxybenzoylacetate (III) in absolute ethyl alcohol in the presence of dry hydrogen chloride gas.The isomeric O,O-diethyl ether of melannein, viz. 6-ethoxy-7-methoxy-4(4'-ethoxy-3'-methoxyphenyl)coumarin (VI) has also been prepared by the condensation of o-methoxyhydroquinone with ethyl p-ethoxy-m-methoxybenzoylacetate (VII).The esters (III), (VII) and (XI) have been prepared by the reaction of the appropriate acetophenone derivatives with diethyl carbonate in the presence of sodium hydride.