Mitsubishi Chemical Industries Limited

Ken-ichi Wakabayashi

Susumu Kanno

Kaoru Fukuda

Yasuhiro Chigira

Steroidal 19-nor-3-hydroxy-1, 3, 5(10)-trienes are produced by a process which comprises admixing a preheated hydrocarbon and a solution of a steroidal 10-methyl-1, 4-diene-3-one dissolved or suspended in a hydrocarbon, and then pyrolyzing said steroidal compound.

Process for producing steroidal compounds

In a process for separating 19-nor-.DELTA..sup.4 -androstene-3,17-dione from a mixture of steroids which is obtained by the Birch reduction of an alkyl or an aralkyl ether of estrone acetal having the following formula (I), ##SPC1## wherein R is selected from the group consisting of an alkyl group containing 1 to 10 carbon atoms and an aralkyl group containing a side chain of 1 to 5 carbon atoms; X and Y are selected from the group consisting of O-alkyl and S-alkyl groups, respectively, containing 1 to 10 carbon atoms; or the following formula (II), ##SPC2## wherein R is as defined above; Z and W are selected from the group consisting of oxygen atom and sulfur atom; and n represents an integer of from 2 to 10; followed by the hydrolysis of the obtained reduction product of said Birch reduction, the improvement which comprises

Process for separation of 19-nor-.DELTA..sup.4 -androstene-3,17-dione

A process for producing a steroid ether which comprises admixing an alkali, a reactant steroid having a hydroxyl group attached directly to an aromatic ring in the steroid nucleus, and a dialkyl sulfate in the presence of at least one hydrophilic solvent in which said reactant and product steroid is readily soluble, selected from the group consisting of cyclic ether and ketone.

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Machida, Japan

Ken-ichi Wakabayashi