# US 11,993,760 B2 · 2-furyl- and 2-thienyl-substituted di- and tetrahydropyrans for use as aroma chemicals

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- Number: US 11,993,760 B2
- Document ID: US11993760B2
- Status: Granted
- Kind: B2
- Application number: 17/059,017
- Filed: 2019-05-24
- Published: 2021-07-08
- Granted: 2024-05-28
- Earliest claimed: 2018-05-25
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Miriam Bru Roig; Manuel Danz; Ralf Pelzer
- Web page: https://patentgrep.com/patent/US11993760B2

## CPC

- C11B 9/0076: {the hetero rings containing less than six atoms}
- C11B 9/008: {the hetero rings containing six atoms}
- A23L 27/2052: {having oxygen or sulfur as the only hetero atoms}
- C07D 407/04: directly linked by a ring-member-to-ring-member bond
- C07D 409/04: directly linked by a ring-member-to-ring-member bond
- 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)
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention relates to the use of 2-furyl- and 2-thienyl-substituted di- and tetrahydropyrans of the formula (I) wherein the variables are as defined in the claims and the description, as aroma chemicals; to aroma chemical compositions comprising at least one 2-furyl- or 2-thienyl-substituted di- or tetrahydropyran and to a method for preparing an aroma chemical composition. The present invention further relates to specific 2-furyl- and 2-thienyl-substituted di- and tetrahydropyrans and to a method for their preparation.

## Claims

### Claim 1

A composition comprising an aroma chemical, wherein the aroma chemical is a compound of the general formula (I)
wherein
X is O or S;
R1 is hydrogen, OH, O—C1-C4-alkyl or O—(C═O)—R5;
R2, R3, R4 are hydrogen;
or one of R2, R3, R4 together with R1 represents a double bond; and
R5 is selected from the group consisting of hydrogen and C1-C4-alkyl;
a mixture of two or more different compounds of the general formula (I), a stereoisomer thereof or a mixture of stereoisomers thereof.

### Claim 2 (depends on 1)

The composition according to claim 1, where the compound of the formula (I) is a compound I-1, I-2 or I-3, where the compound I-1 is a compound of the formula (I) in which R2 together with R1 represents a double bond, the compound I-2 is a compound of the formula (I) in which R3 together with R1 represents a double bond and the compound I-3 is a compound of the formula (I) in which R4 together with R1 represents a double bond; or is a mixture of at least two compounds I-1, I-2 and I-3.

### Claim 3 (depends on 2)

The composition according to claim 2, where the mixture contains compounds I-2 and I-3 and optionally also compound I-1, where compound I-1 is contained in an amount of from 0 to 10% by weight, compound I-2 is contained in an amount of from 1 to 80% by weight, and compound I-3 is contained in an amount of from 15 to 99% by weight, relative to the total weight of compounds I-1, I-2 and I-3.

### Claim 4 (depends on 1)

The composition according to claim 1, where in formula (I) R1 is hydrogen.

### Claim 5 (depends on 1)

The composition according to claim 1, where in formula (I) R1 is OH.

### Claim 6 (depends on 1)

The composition according to claim 1, where in formula (I) R1 is O—C1-C4-alkyl.

### Claim 7 (depends on 1)

The composition according to claim 1, where in formula (I) R1 is O—(C═O)—R5.

### Claim 8 (depends on 1)

The composition according to claim 1, where X is O.

### Claim 9 (depends on 1)

The composition according claim 1, where X is S.

### Claim 10 (depends on 1)

The composition according to claim 1, wherein the composition imparts an olfactory impression.

### Claim 11 (depends on 10)

The composition according to claim 10, wherein the composition is a fragrance.

### Claim 12 (depends on 1)

A fragranced ready-to-use composition comprising a compound of general formula (I) as defined in claim 1, a stereoisomer thereof, a mixture of stereoisomers thereof or a mixture of different compounds of the general formula (I) as defined in claim 1, for modifying the scent character of the fragranced ready-to-use composition.

### Claim 13 (depends on 1)

The composition according to claim 1, wherein the composition is selected from perfume compositions, body care compositions, products for oral and dental hygiene, hygiene articles, cleaning compositions, textile detergent compositions, compositions for scent dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions.

### Claim 14 (depends on 1)

A composition comprising at least one compound of the general formula (I) as defined in claim 1, a mixture thereof, a stereoisomer thereof or a mixture of stereoisomers of at least one compound of the general formula (I) as defined in claim 1, and at least one further compound selected from the group consisting of aroma chemicals different from compounds of the general formula (I) and non-aroma chemical carriers.

### Claim 15 (depends on 14)

The composition according to claim 14, where the non-aroma chemical carriers are selected from the group consisting of surfactants, emollients and solvents, where the solvents are selected from the group consisting of ethanol, isopropanol, propylene glycol, dipropylene glycol, 1,2-butylene glycol, diethylene glycol monoethyl ether, glycerol, diethyl phthalate, isopropyl myristate, triethyl citrate, and benzyl benzoate.

### Claim 16 (depends on 14)

The composition according to claim 14, which is selected from the group consisting of perfume compositions, body care compositions, products for oral and dental hygiene, hygiene articles, cleaning compositions, textile detergent compositions, compositions for scent dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions.

### Claim 17

A compound of the general formula (I.a)
wherein
R1 is hydrogen, OH, O—C1-C4-alkyl or O—(C═O)—R5,
R5 is selected from the group consisting of hydrogen and C1-C4-alkyl;
a mixture thereof, a stereoisomer thereof or a mixture of stereoisomers thereof.

### Claim 18 (depends on 17)

The compound according to claim 17, wherein R1 is OH, O—C1-C4-alkyl or O—(C═O)—R5.

### Claim 19

A compound of the general formula (I.b)
wherein
R1 is hydrogen, OH, O—C1-C4-alkyl or O—(C═O)—R5,
R2, R3, R4 are hydrogen;
or one of R2, R3, R4 together with R1 represents a double bond;
R5 is selected from the group consisting of hydrogen and C1-C4-alkyl;
a mixture thereof, a stereoisomer thereof or a mixture of stereoisomers thereof.

### Claim 20 (depends on 1)

A mixture of at least two different compounds of formula (I) as defined in claim 1; where the mixture is a mixture of a least two compounds I-1, I-2 and I-3, where in compound I-1 R2 together with R1 represents a double bond, in compound I-2 R3 together with R1 represents a double bond, and in compound I-3 R4 together with R1 represents a double bond.

### Claim 21 (depends on 20)

The mixture according to claim 20, where X is S.

### Claim 22 (depends on 20)

The mixture according to claim 20, where the mixture contains compounds I-2 and I-3 and optionally also compound I-1, where compound I-1 is contained in an amount of from 0 to 10% by weight, compound I-2 is contained in an amount of from 1 to 80% by weight, and compound I-3 is contained in an amount of from 15 to 99% by weight, relative to the total weight of compounds I-1, I-2 and I-3.

### Claim 23 (depends on 1, 17)

A method for preparing the compound of formula (I.a) according to claim 17, or a mixture of different compounds (I.a), which method comprises: for preparing the compound of formula (I.a) where R1 is OH or H or a mixture thereof:
(i) reacting 3-methylbut-3-en-1-ol with furan-2-carbaldehyde in the presence of a Brønsted acid to obtain a crude product mixture containing a compound of the formula (I) as defined in claim 1, where X is O and R1 is OH, and one or more of compounds of formula (I), where X is O and one of R2, R3, R4 together with R1 represents a double bond; and
(ii) optionally isolating the compound of formula (I), where X is O and R1 is OH; or, alternatively to step (ii),
(iii) optionally separating the compounds of formula (I), where X is O and one of R2, R3, R4 together with R1 represents a double bond, from the compound of formula (I), where X is O and R1 is OH, and subjecting the compounds of formula (I), where one of R2, R3, R4 together with R1 represents a double bond, to a hydrogenation reaction; or, alternatively to steps (ii) and (iii),
(iv) optionally subjecting the crude product mixture obtained in step (i) to a hydrogenation reaction and optionally isolating the compound of formula (I), where X is O and R1 is H;
and for preparing the compound of formula (I.a), where R1 is O—C1-C4-alkyl or O—(C═O)—R5:
(v) subjecting the compound of formula (I.a), where R1 is OH, to an alkylation or acylation reaction.

### Claim 24 (depends on 19)

A method for preparing the compound of formula (I.b) according to claim 19, or a mixture of different compounds of formula (I.b), which method comprises
(i′) reacting 3-methylbut-3-en-1-ol with thiophene-2-carbaldehyde in the presence of a Brønsted acid to obtain a crude product mixture containing a compound of the formula (I.b) where R1 is OH, and one or more of compounds of formula (I.b) where one of R2, R3, R4 together with R1 represents a double bond,
(ii′) optionally isolating the compound of formula (I.b), where R1 is OH; or, alternatively to step (ii′),
(iii′) optionally separating the compounds of formula (I.b), where one of R2, R3, R4 together with R1 represents a double bond, from the compound of formula (I.b) where R1 is OH and, if desired, subjecting the compounds of formula (I.b), where one of R2, R3, R4 together with R1 represents a double bond, to a hydrogenation reaction; or, alternatively to steps (ii′) and (iii′),
(iv′) optionally subjecting the crude product mixture obtained in step (i) to a hydrogenation reaction and optionally isolating the compound of formula (I.b), where R1 is H; or, alternatively to steps (iii′) and (iv′),
(v′) optionally subjecting the compound of formula (I.b), where R1 is OH, to an alkylation or acylation reaction.

### Claim 25

A mixture of at least two different compounds of formula (I)
wherein
X is S;
R1 is hydrogen, OH, O—C1-C4-alkyl or O—(C═O)—R5;
R2, R3, R4 are hydrogen;
or one of R2, R3, R4 together with R1 represents a double bond; and
R5 is selected from the group consisting of hydrogen and C1-C4-alkyl.