Novel hydroperoxide and use of same as intermediate for the preparation of 3a,6,69a-tetramethylperhydronaphtho[2,1-b]furan
AssigneeFirmenich SA
InventorsGeorge M. Whitesides, Rene Decorzant, Ferdinand Naef
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Abstract
Novel hydroperoxide of formula ##STR1## and use of same as intermediate for the preparation of 3a,6,6,9a-tetramethylperhydronaphtho[2,1-b]furan, also known as AMBROX (registered tradename of FIRMENICH SA, Geneva/Switzerland). Process for its preparation via an oxidation of sclareol by means of hydrogen peroxide in the presence of an acidic agent.
Claims12
A process for the preparation of 3a,6,6,9a-tetramethylperhydronaphtho[2,1b]furan, which comprises treating an epimeric mixture of hydroperoxides of the formula:
- ##STR10## with a redox reagent consisting of the couple Fe.sup.II /Cu.sup.II to form ##STR11##
A process for the preparation of 3,a,6,6,9a-tetramethylperhydronaphtho[2,1-b]furan, which comprises treating an epimeric mixture of the formula:
- ##STR12## with a redox reagent of the couple Fe(II) sulphate/Cu(II) acetate in an alcoholic medium to form ##STR13##
A process for the preparation of 3a,6,6,9a-tetramethylperhydronaphtho(2,1-b)furan, which comprises:
- oxidizing sclareol with hydrogen peroxide having a concentration of greater than 50% (v/v) in water in the presence of an acidic agent of p-toluene-sulfonic acid to form an epimeric mixture of hydroperoxides of the formula:
- ##STR14## separating the epimeric mixture of hydroperoxides from the reaction mixture by column chromatography;
- and
- treating the epimeric mixture of hydroperoxides with a refox reagent consisting of the couple Fe.sup.II /Cu.sup.II in an alcoholic medium to form ##STR15##
Dependencies are inferred from the claim text.