# US 10,865,173 B2 · Organic compounds

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- Number: US 10,865,173 B2
- Document ID: US10865173B2
- Status: Granted
- Kind: B2
- Application number: 16/765,235
- Filed: 2018-12-03
- Published: 2020-09-10
- Granted: 2020-12-15
- Earliest claimed: 2017-12-05
- Assignees: Givaudan SA
- Applicants: Givaudan SA
- Inventors: Fridtjof Schröder; Nicole Pfeiffer
- Web page: https://patentgrep.com/patent/US10865173B2

## CPC

- C07C 45/34: in unsaturated compounds
- B01J 31/1815: {with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine}
- B01J 35/39: Photocatalytic properties
- B01J 2231/005: General concepts, e.g. reviews, relating to methods of using catalyst systems, the concept being defined by a common method or theory, e.g. microwave heating or multiple stereoselectivity
- B01J 2231/70: Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
- B01J 2531/842: Iron
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

An allylic oxidation process includes forming a mixture containing α-Guaiene and an iron (III)-X porphyrin complex catalyst in a sustainable solvent, introducing molecular oxygen into the mixture, and effecting allylic oxidation to produce an α,ß-unsaturated ketone, Rotundone.

## Claims

### Claim 1

An allylic oxidation process comprising:
forming a mixture containing a-Guaiene and an iron (III)-X porphyrin complex catalyst, wherein X is selected from the group consisting of CI, Br, I, mesylates, triflates, and carboxylates, in a sustainable solvent,
introducing molecular oxygen into the mixture, and
effecting allylic oxidation to produce an α,ß-unsaturated ketone, Rotundone.

### Claim 2 (depends on 1)

The process according to claim 1, wherein the mixture additionally contains a base coordination compound.

### Claim 3 (depends on 1)

The process according to claim 1, including exposing the mixture to electromagnetic radiation.

### Claim 4 (depends on 1)

The process according to claim 1, wherein the sustainable solvent is selected from the group consisting of water, acetone, ethanol, 2-propanol, ethyl acetate, isopropyl acetate, methanol, methyl ethyl ketone, 1-butanol, t-butanol and mixtures thereof.

### Claim 5 (depends on 1)

The process according to claim 1, wherein the sustainable solvent is selected from the group consisting of cyclohexane, heptane, toluene, methylcyclohexane, methyl t-butyl ether, isooctane, acetonitrile, xylenes, dimethyl sulfoxide, acetic acid, ethylene glycol and mixtures thereof.

### Claim 6 (depends on 1)

The process according to claim 1, wherein the catalyst is an iron (III) porphyrin complex catalyst, having a chloride counter-ion.

### Claim 7 (depends on 1)

The process according to claim 1, wherein the porphyrin complex is a tetraphenylporphyrin complex.

### Claim 8 (depends on 1)

The process according to claim 1, wherein the catalyst is selected from chloro(tetraphenylporphyrinato)iron(III) and hemin chloride.

### Claim 9 (depends on 2)

The process according to claim 2, including exposing the mixture to electromagnetic radiation.

### Claim 10 (depends on 4)

The process according to claim 4, wherein the sustainable solvent is selected from the group consisting of cyclohexane, heptane, toluene, methylcyclohexane, methyl t-butyl ether, isooctane, acetonitrile, xylenes, dimethyl sulfoxide, acetic acid, ethylene glycol and mixtures thereof.

### Claim 11 (depends on 2)

The process according to claim 2, wherein the catalyst is an iron (III) porphyrin complex catalyst, having a chloride counter-ion.

### Claim 12 (depends on 3)

The process according to claim 3, wherein the catalyst is an iron (III) porphyrin complex catalyst, having a chloride counter-ion.

### Claim 13 (depends on 4)

The process according to claim 4, wherein the catalyst is an iron (III) porphyrin complex catalyst, having a chloride counter-ion.

### Claim 14 (depends on 5)

The process according to claim 5, wherein the catalyst is an iron (III) porphyrin complex catalyst, having a chloride counter-ion.

### Claim 15 (depends on 11)

The process according to claim 11, wherein the porphyrin complex is a tetraphenylporphyrin complex.

### Claim 16 (depends on 12)

The process according to claim 12, wherein the porphyrin complex is a tetraphenylporphyrin complex.

### Claim 17 (depends on 13)

The process according to claim 13, wherein the porphyrin complex is a tetraphenylporphyrin complex.

### Claim 18 (depends on 14)

The process according to claim 14, wherein the porphyrin complex is a tetraphenylporphyrin complex.

### Claim 19 (depends on 2)

The process according to claim 2, wherein the catalyst is selected from chloro(tetraphenylporphyrinato)iron(III) and hem in chloride.

### Claim 20 (depends on 3)

The process according to claim 3, wherein the catalyst is selected from chloro(tetraphenylporphyrinato)iron(III) and hem in chloride.

### Claim 21 (depends on 4)

The process according to claim 4, wherein the catalyst is selected from chloro(tetraphenylporphyrinato)iron(III) and hem in chloride.

### Claim 22 (depends on 5)

The process according to claim 5, wherein the catalyst is selected from chloro(tetraphenylporphyrinato)iron(III) and hem in chloride.

### Claim 23 (depends on 6)

The process according to claim 6, wherein the catalyst is selected from chloro(tetraphenylporphyrinato)iron(III) and hem in chloride.