Process for the manufacture of known odorants

US5329053A · kind A · utility

Assignee

• Givaudan-Roure Corporation · US

Inventor

• Daniel Helmlinger · Stintenberger Straße, CH

Key dates

• Filing date: Aug 25, 1993
• Grant date: Jul 12, 1994
• Expiry date: Aug 25, 2013

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C2601/16
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

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 aforeme…