Firmenich Sa

Massachusetts Institute of Technology

George H Buchi

Hans Wuest

Gunther Ohloff

Hugo Strickler

Arnold Hauser

John Christopher Vederas

Roger M Freidinger

3a,6,6,9a-Tetramethylperhydronaphto[2,1-b]furan, a typical ambergris perfume ingredient is prepared via a novel process from 1.beta.-(2-hydroxyethyl)-perhydro-2,5,5,8a.beta.-tetramethyl-2.beta.-trans -napthalenol by cyclization with an acidic cyclization agent in the presence of nitromethane.

Process for the preparation of

3a,6,6,9a-Tetramethylperhydronaphto[2,1-b]furan, a typical ambergris perfume ingredient is prepared via a novel process from 1.beta.-(2-hydroxyethyl)-perhydro-2,5,5,8a.beta.-tetramethyl-2.beta.-trans -naphthalenol by cyclization with an acidic cyclization agent in the presence of nitromethane.

New unsaturated macrocyclic ketones are obtained via a process which consists in reacting a dialdehyde with a tetraalkyldiphosphonate ester. The new ketones are useful intermediates for the preparation of cyclopentadecanone and its higher methyl-homologue, known fragrant substances. New ketones possess also direct utility as musky odorants.

Process for the preparation of novel unsaturated macrocyclic ketones

9-Hydroxy-undeca-4,10-dien-1-al, a novel unsaturated aliphatic hydroxy-aldehyde, has been found to possess useful odorous properties and consequently can be advantageously used as perfume ingredient.

9-Hydroxy-undeca-4,10-dien-1-al

Novel tricyclo-ketone derivatives useful as perfume ingredients and as intermediates for the preparation of (.+-.) khusimone.

6,6,7-Trimethyl-tricyclo[5.2.2.0.sup.1,5 ]undec-8-en-2-one

New cycloaliphatic unsaturated ketones and their use as perfuming and odor-modifying agents in the manufacture of perfumes and perfumed products, and as flavoring and taste-modifying agents in the preparation of foodstuffs in general and imitation flavors for foodstuffs, beverages, animal feeds, pharmaceutical preparations and tobacco products. Methods for preparing the said new compounds and certain of the starting materials used for their synthesis.

Cycloaliphatic unsaturated ketones as fragrance modifying agents

The invention provides a method for the preparation of 2-cyclopenten-1-one derivatives. The process involves metalating 2-methylfuran in the 5-position by an interchange reaction with an alkali metal-organic compound, condensing the resulting metal derivative of 2-methylfuran with a halide of the formula R--CH.sub.2 --X, wherein R represents an unsubstituted acyclic hydrocarbon radical which is free of triple bonds, comprises from 0 to 2 double bonds and contains from 3 to 5 carbon atoms and X represents a halogen, in order to form a 2,5-disubstituted furan of the formula ##EQU1## treating the disubstituted furan with an acidic agent to cause the opening of the furan ring and the formation of a dione of the formula ##EQU2## and cyclizing the dione by a treatment with alkali. The invention also provides certain novel 2-cyclopenten-1-one derivatives which are useful as fragrant ingredients in the manufacture of perfume compositions and which constitute valuable starting materials in the manufacture of other useful organic compounds.

Method for preparing cyclopentenone derivatives

The present invention relates to a novel process for preparing unsaturated aldehydes comprising four double bonds of formula ##SPC1## Wherein one of the double bonds is represented by the dotted lines. Aldehyde Ia (called .alpha.-sinensal) corresponds to the above formula wherein the double bond represented by the dotted lines is in the main carbon chain. Aldehyde Ib (called .beta.-sinensal) corresponds to the above formula wherein the double bond represented by the dotted lines is in the side chain. The invention also relates to new intermediates used in the said new process and to methods for preparing them. The said intermediates have also valuable organoleptic properties and are useful as fragrances in the preparation of perfumes, perfumed products and artificial essential oils.

Process for the preparation of unsaturated aldehydes

Process for the preparation of unsaturated aldehydes, in particular .gamma.,.delta.-unsaturated aldehydes, which comprises reacting an amino-nitrile with a basic or a neutral agent. The products obtained in accordance with the process of the invention are useful intermediates for the preparation of flavoring ingredients.

4-Methyl-8-vinyl-4,7- and -4,8-nonadienals

New process for the preparation of cyclic ketones possessing interesting organoleptic properties and including methyl 2-(cis-pent-2-enyl)-3-oxo-cyclopentylacetate and 3-methyl-2-(cis-pent-2-enyl)-cyclopent-2-enone, better known in the perfume industry as cis-methyl jasmonate and cis-jasmone respectively.

Process for the preparation of cyclic ketones

Polyenes are synthesized from unsaturated materials having allylic hydroxyl groups, which react with imidosulfides to produce sulfones. Removal of the sulfone group, e.g. by reaction with alkyllithium and iodine, results in compounds in which the allylic carbons are joined by a double bond. The reactions take place easily over wide temperature ranges. The method is particularly advantageous in the synthesis of carotenoids from polyene alcohols, being much simpler and easier to use than previous carotenoid syntheses.

Preparation of polyenes

New heterocyclic derivatives containing nitrogen useful for perfumery and the flavour industry and use of same as perfuming and/or flavouring ingredients in the manufacture of perfumes and perfumed products and/or in the preparation of artificial flavours for foodstuffs, beverages, animal feeds, pharmaceutical preparations and tobacco products. Process for preparing the said heterocyclic derivatives which are equally useful as starting materials for preparing known fragrance compounds.

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Cambridge, MA, United States of America

George H Buchi