Process for preparing tricyclic alcohols

Claim 2

A process for producing a compound having the structure: ##STR39## wherein each of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is the same or different and represents hydrogen or methyl and wherein the dashed line represents a carbon-carbon single bond when one of R 2 or R 3 is hydrogen or a carbon-carbon double bond when R 2 and R 3 are each methyl comprising the steps of: (a) Intimately admixing at a temperature in the range of 170°-260° C. at autogeneous pressure a methyl-substituted cyclohexadienone having the structure: ##STR40## with an acetylenic compound having the structure: ##STR41## the mole ratio of methyl-substituted cyclohexadienone:acetylenic compound being 1:1, where X is selected from the group consisting of chloro and bromo thereby forming a diene compound having the structure: ##STR42## (b) Hydrogenating the diene compound at a temperature in the range of 100°-200° C. and a pressure of 5-15 atmospheres with hydrogen in the presence of a hydrogenation catalyst selected from the group consisting of palladium, platinum and nickel thereby producing a ketone having the structure: ##STR43## and (c) Cyclizing the ketone thus formed by treating said ketone with an alkali metal selected from the group consisting of sodium, lithium and potassium in a solvent selected from the group consisting of diethyl ether, tetrahydrofuran and benzene, the mole ratio of ketone:metal being from 1:1 up to 10:1.

Claim 3

The process of claim 1 wherein each of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is hydrogen and the dashed line is a carbon-carbon single bond.

Claim 4

The process of claim 1 wherein R 1 is methyl and R 2 , R 3 , R 4 , R 5 and R 6 is hydrogen.

Claim 5

The process of claim 1 wherein X is chloro.

Claim 6

The process of claim 1 wherein the dashed line is a carbon-carbon single bond.

Claim 7

The process for preparing a compound having the structure: ##STR44## wherein the dashed line is either a carbon-carbon single bond or a carbon-carbon double bond; wherein each of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is hydrogen or methyl; wherein the dashed line is a carbon-carbon single bond when one of R 2 or R 3 is hydrogen and wherein the dashed line is a carbon-carbon double bond when each of R 2 and R 3 is methyl comprising the steps of: (a) Intimately admixing at a temperature in the range of 170°-260° C. at autogenous pressure a cyclohexadienone having the structure: ##STR45## with an acetylenic compound having the structure: ##STR46## the mole ratio of cyclohexadienone: acetylenic compound being 1:1, thereby forming a diene compound having the structure: ##STR47## (b) Hydrogenating said diene compound at a temperature in the range of 100°-200° C. and a pressure of 5-15 atmospheres with hydrogen in the presence of a hydrogenation catalyst selected from the group consisting of palladium, platinum and nickel thereby forming a ketone having the structure: ##STR48## (c) Intimately admixing said ketone with a halogenating agent selected from the group consisting of thionyl chloride, thionyl chloride-pyridine-tri-bromide, aqueous HCl and aqueous HBr at a temperature in the range from 20° C. up to 100° C. thereby forming a haloalkyl ketone having the structure: ##STR49## (d) Cyclizing said haloalkyl ketone with a cyclizing agent selected from the group consisting of sodium, potassium and lithium in a solvent selected from the group consisting of diethyl ether, tetrahydrofuran and benzene, the mole ratio of ketone:metal being from 1:1 up to 10:1.

Claim 8

The process for preparing a compound having the structure: ##STR44## wherein the dashed line is either a carbon-carbon single bond or a carbon-carbon double bond; wherein each of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is hydrogen or methyl; wherein the dashed line is a carbon-carbon single bond when one of R 2 or R 3 is hydrogen and wherein the dashed line is a carbon-carbon double bond when each of R 2 and R 3 is methyl comprising the steps of: (a) Intimately admixing at a temperature in the range of 170°-260° C. at autogenous pressure a cyclohexadienone having the structure: ##STR45## with an acetylenic compound having the structure: ##STR46## the mole ratio of cyclohexadienone: acetylenic compound being 1:1, thereby forming a diene compound having the structure: ##STR47## (b) Hydrogenating said diene compound at a temperature in the range of 100°-200° C. and a pressure of 5-15 atmospheres with hydrogen in the presence of a hydrogenation catalyst selected from the group consisting of palladium, platinum and nickel thereby forming a ketone having the structure: ##STR48## (c) Intimately admixing said ketone with a halogenating agent selected from the group consisting of thionyl chloride, thionyl chloride-pyridine-tri-bromide, aqueous HCl and aqueous HBr at a temperature in the range from 20° C. up to 100° C. thereby forming a haloalkyl ketone having the structure: ##STR49## (d) Cyclizing said haloalkyl ketone with a cyclizing agent selected from the group consisting of sodium, potassium and lithium in a solvent selected from the group consisting of diethyl ether, tetrahydrofuran and benzene, the mole ratio of ketone:metal being from 1:1 up to 10:1.

Claim 9

The process of claim 6 wherein each of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is hydrogen.

Claim 10

The process of claim 6 wherein R 1 is methyl and each of R 2 , R 3 , R 4 , R 5 and R 6 is hydrogen.

Claim 11

The process of claim 6 wherein X is chloro.