# US 2022/0033338 A1 · 2-(5-isopropyl-2-methyl-cyclohex-2-en- 1-yl-)acetaldehyde and 2-(6-isopropyl- 3-methyl-cyclohex-2-en-1-yl-) acetaldehyde as new odorants > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2022/0033338 A1 - Document ID: US20220033338A1 - Status: Published application - Kind: A1 - Application number: 17/276,442 - Filed: 2018-09-19 - Published: 2022-02-03 - Earliest claimed: 2018-09-19 - Assignees: Symrise AG - Applicants: Symrise AG - Inventors: Bernd Hoelscher; Frank Gerstmann; Mark Mansfeld - Web page: https://patentgrep.com/patent/US20220033338A1 ## CPC - C07C 47/225: containing rings other than six-membered aromatic rings - A61K 8/33: containing oxygen - A61Q 13/00: Formulations or additives for perfume preparations (essential oils or perfumes per se C11B9/00) - C11B 9/0034: {the ring containing six carbon atoms} - C11B 9/0061: {compounds containing a six-membered aromatic ring not condensed with another ring} - A61K 2800/591: Mixtures of compounds not provided for by any of the codes A61K2800/592 - A61K2800/596 - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS - C11B: PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES (drying-oils C09F) ## Abstract The present invention relates to novel compounds of formula (I) as well as mixtures comprising or consisting of compounds of formula (I). Furthermore, the present invention relates to a process for the preparation of the compounds of formula (I) and to the use of the compounds of formula (I) as a perfuming ingredient, in particular as a lily of the valley perfuming ingredient. Ultimately, the present invention relates to perfume preparations and perfumed products or consumer goods comprising at least one of the compounds of formula (I). ## Claims ### Claim 1 A compound of formula (I) wherein R1 is H or —CH2—CHO, and R2 is H or —CH2—CHO, with the proviso that R1≠R2; and stereoisomers or mixtures thereof. ### Claim 2 (depends on 1) A compound according to claim 1, wherein the compound of formula (I) is represented by the following formula (II) or formula (III): or a stereoisomer thereof, or a mixture thereof. ### Claim 3 (depends on 2) A compound according to claim 2, wherein the compound of formula (II) is represented by the following formula (IIa) or formula (IIb): or a mixture thereof. ### Claim 4 (depends on 2) A compound according to claim 2, wherein the compound of formula (III) is represented by the following formula (IIIa) or formula (IIIb): or a mixture thereof. ### Claim 5 (depends on 2) A mixture comprising (a) at least one compound of formula (II) or a stereoisomer thereof, and (b) at least one compound of formula (III) or a stereoisomer thereof according to claim 2. ### Claim 6 (depends on 1) A process for preparing a compound of formula (I) or formula (II) according to claim 1, comprising the following steps: (i) acid reaction of the compound 2-methyl-5-(1-methylethyl-)2-cyclohexen-1-ol (IV) with at least one vinyl ether (R—O) to give an acetal (V); (ii) cleavage of the acetal (V) obtained in step (i) by acid catalysis into a vinyl ether (VI); and (iii) thermal conversion of the vinyl ether (VI) obtained in step (ii) into the aldehyde (II); according to the following reaction scheme: ### Claim 7 (depends on 1) A process for preparing a compound of formula (I) or formula (II) according to claim 1, comprising the following steps: (i) acid reaction of the compound 2-methyl-5-(1-methylethenyl-)2-cyclohexen-1-ol (VII) with at least one vinyl ether (R—O) to give an acetal (VIII); (ii) cleavage of the acetal (VIII) obtained in step (iv) by acid catalysis into a vinyl ether (IX); (iii) thermal conversion of the vinyl ether (IX) obtained in step (v) into the aldehyde (X); and (iv) hydrogenation of the terminal double bond to give the aldehyde (II); according to the following reaction scheme: ### Claim 8 (depends on 1) A process for preparing a compound of formula (I) or formula (III) according to claim 1, comprising the following steps: (i) acid reaction of the compound 1-methyl-4-(1-methylethyl-)2-cyclohexen-1-ol (XI) with at least one vinyl ether (R—O) to give an acetal (XII); (ii) cleaving the acetal (XII) obtained in step (vii) by acid catalysis into a vinyl ether (XIII); and (iii) thermal conversion of the vinyl ether (XIII) obtained in step (viii) into the aldehyde (III); according to the following reaction scheme: ### Claim 9 (depends on 1) A process for preparing a compound of formula (I) or formula (III) according to claim 1, comprising the following steps: (i) acid reaction of the compound 1-methyl-4-(1-methylethenyl-)2-cyclohexen-1-ol (XX) with at least one vinyl ether (R—O) to give an acetal (XXI); (ii) cleavage of the acetal (XXI) obtained in step (vii) by acid catalysis into a vinyl ether (XXII); (iii) thermal conversion of the vinyl ether (XXII) obtained in step (viii) into the aldehyde (XXIII); and (iv) hydrogenation of the terminal double bond to give the aldehyde (III); according to the following reaction scheme: ### Claim 10 (depends on 6) A process for preparing a compound of formula (II) or a compound of formula (III) according to claim 6, wherein the radical R of the vinyl ether (R—O) in step (i) is selected from the group consisting of linear C1 to C20 alkyl radical, branched C1 to C20 alkyl radical, cyclopentyl radical and cyclohexyl radical. ### Claim 11 (depends on 1) A method of using at least one compound of the formula (I) or a stereoisomer thereof or a mixture of the compounds of the formula (I) or stereoisomers thereof according to claim 1, comprising using the compound as a perfume or for the preparation of a perfume composition. ### Claim 12 (depends on 1) A perfume or perfume preparation comprising at least one compound of formula (I) or a stereoisomer thereof according to claim 1. ### Claim 13 (depends on 12) A perfume preparation according to claim 12, further comprising one or more additional perfume(s) and/or aroma(s), wherein said one or more additional perfume(s) and/or aroma(s) is/are selected from one or more in the group of: extracts of natural raw materials, preferably essential oils, concretes, absolues, resins, resinoids, balsams, tinctures and/or single odorants, preferably from the group of hydrocarbons, aliphatic alcohols, aliphatic aldehydes and their acetals, aliphatic ketones and their oximes, aliphatic sulfur-containing compounds, aliphatic nitriles, esters of aliphatic carboxylic acids, acyclic terpene alcohols, acyclic terpene aldehydes and ketones, cyclic terpene alcohols, cyclic terpene aldehydes and ketones, cyclic alcohols, cycloaliphatic alcohols, cyclic and cycloaliphatic ethers, cyclic and macrocyclic ketones, cycloaliphatic aldehydes, cycloaliphatic ketones, esters of cyclic alcohols, esters of cycloaliphatic alcohols, aliphatic alcohols, esters of aliphatic alcohols and aliphatic carboxylic acids, aliphatic ethers, aromatic and aliphatic aldehydes, aromatic and aliphatic ketones, aromatic and aliphatic carboxylic acids and their esters, nitrogen-containing aromatic compounds, phenols, phenyl ethers and phenyl esters, heterocyclic compounds, and lactones. ### Claim 14 (depends on 1, 12) The perfume preparation according to claim 12, wherein the total amount of the one or more compounds of formula (I) according to claim 1 is 0.00001 to 5% by weight, based on the total weight of the perfume preparation. ### Claim 15 (depends on 12) A perfumed product comprising a fragrance or a fragrance preparation according to claim 12, and a supplement. ### Claim 16 (depends on 15) A perfumed product according to claim 15, comprising one or more additives selected from the group of: preservatives, abrasives, anti-acne agents, anti-aging agents, anti-bacterial agents, anti-cellulitis agents, anti-dandruff agents, anti-inflammatory agents, anti-irritant agents, anti-irritant agents, antimicrobial agents, antioxidants, astringents, antiperspirants, antiseptics, antistatics, binders, buffers, carriers, chelating agents, cell stimulants, cleansing agents, conditioning agents, depilatories, surfactants, deodorizers, antiperspirants, emollients, emulsifiers, enzymes, essential oils, fibers, film formers, fixatives, foaming agents, foam stabilizers, anti-foaming substances, foam boosters, fungicides, gelling agents, gelling agents, hair care agents, hair shaping agents, hair smoothing agents, moisturizing agents, moistening substances, moisture retaining substances, bleaching agents, strengthening agents, stain removing agents, optical brightening agents, impregnating agents, soil-repellent agents, friction-reducing agents, lubricants, moisturizers, ointments, opacifiers, plasticizing agents, covering agents, polishes, brighteners, polymers, powders, proteins, refatting agents, abrasive agents, silicones, skin soothing agents, skin cleansing agents, skin conditioning agents, skin healing agents, skin whitening agents, skin protecting agents, skin softening agents, cooling agents, skin cooling agents, warming agents, skin warming agents, stabilizers, UV absorbing agents, UV filters, detergents, fabric softeners, suspending agents, skin tanning agents, thickening agents, vitamins, oils, waxes, fats, phospholipids, saturated fatty acids, mono- or polyunsaturated fatty acids, α-hydroxy acids, polyhydroxy fatty acids, liquefiers, dyes, color-protecting agents, pigments, anti-corrosives, aromas, flavors, fragrances, polyols, surfactants, electrolytes, organic solvents or silicone derivatives. ### Claim 17 (depends on 15) The perfumed product according to claim 15, wherein the product is one selected from the group consisting of: detergents and cleaning products, hygiene or care products, especially in the field of body and hair care, cosmetics, of the household, fine fragrances (perfumes), air care and air fresheners. ### Claim 18 (depends on 2) A compound according to claim 2, wherein the compound of formula (I) is a diastereomer of a compound of formula (II) or formula (III). ### Claim 19 (depends on 2) A compound according to claim 2, wherein the compound of formula (I) is an enantiomer of a compound of formula (II) or formula (III). ### Claim 20 (depends on 1, 12) The perfume preparation according to claim 12, wherein the total amount of the one or more compounds of formula (I) according to claim 1 is 0.00001 to 1% by weight, based on the total weight of the perfume preparation.