Imc Chemical Group, Inc.

Commercial Solvents Corporation

Wilbert Herbert Urry

Frank Kavka

Donald E Robertson

Guy Towns Mullenbach

A method is disclosed for preparing dideoxyzearalane and related compounds which comprises reacting a hexahydrozearalin with an organic sulfonyl chloride to form a sulfonate ester derivative; recovering the sulfonate ester derivative; and catalytically dehydrosulfonyloxylating and aromatizing the sulfonate ester derivative to form the desired product.

Synthesis of dideoxyzearalane and related compounds

This invention provides a new synthesis for zearalanone and for related compounds having more or fewer carbon atoms in the non-aromatic ring than does zearalanone, which related compounds and zearalanone are represented by the formula ##SPC1## Wherein X is an integer having a value from 2 to 6 inclusive and Y is an integer having a value from 2 to 8 inclusive. It also provides for new methods of making compounds useful in the synthesis of zearalanone and related compounds. The new compounds useful as intermediates are 2,7-octadienoic acid; methyl 2,7-octadienoate; sodium ethyl 6-(4-pentenyl)-.beta.-dihydroresorcylate; ethyl 6-(4-pentenyl)-.beta.-dihydroresorcylate; sodium methyl 6-(4-pentenyl)-.beta.-dihydroresorcylate; methyl 6-(4-pentenyl)-.beta.-dihydroresorcylate; methyl 3-bromo-6-(4-pentenyl)-.beta.-dihydroresorcylate; methyl 6-(4-pentenyl)-.beta.-resorcylate; ethyl 6-(4-pentenyl)-.beta.-resorcylate; ethyl 6-(4-pentenyl)-.beta.-resorcylate dibenzyl ether; and 4-penten-2-yl 6-(4-pentenyl)-.beta.-resorcylate dibenzyl ether.

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Chicago, IL, United States of America

Wilbert Herbert Urry