Process for the manufacture of known odorants

Details Process for the manufacture of known odorants Process for the manufacture of known odorants

1993-08-25

1994-07-12

Lone, Werren B.

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

568822, 568823, 568825, C07C 3314

Patent

active

053290534

ABSTRACT:
A novel process is described for the manufacture of a mixture of 6-(2',6',6'-trimethyl-cyclohex-1'-en-1'-yl)-4-methyl-hex-3-en-1-ol and -4-en-1-ol (I) and, respectively, of a mixture of [3a.alpha.,5a.beta.,9a.alpha.,9b.beta.]-dodecahydro-3a,6,6,9a-tetramethyln aphtho[2,1-b]furan and [3a.alpha.,5a.beta.,9a.alpha.,9b.alpha.]-dodecahydro-3a,6,6,9a-tetramethyl naphtho[2,1-b]furan, in which E,E-6-(2',6',6'-trimethylcyclohex-1'-en-1'-yl)-4-methyl-hexa-2,4-dien-1-al is reduced either with (a) lithium aluminium hydride or with (b) sodium dithionite in the presence of sodium bicarbonate in aqueous solution and of a phase transfer catalyst or with (c) sodium borohydride or with (d) sodium bis(2-methoxyethoxy)aluminium dihydride and, when reduction agent (c) or (d) is used and optionally in the case when reduction agent (a) is used, the E,E-6-(2',6',6'-trimethyl-cyclohex-1'-en-1'-yl)-4-methyl-hexa-2,4-dien-1-o l which results as the intermediate is reduced to the desired 6-(2',6',6'-trimethyl-cyclohex-1'-en-1'-yl)-4-methyl-hex-3-en-1-ol and -4-en-1-ol using a reduction agent (a) or (b) and, if desired, the thus-obtained compounds I are converted in a known manner into a mixture of the aforementioned furans. These furans are suitable as odorants.

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