# US 11,306,050 B2 · Methods of synthesizing cannabigergol, cannabigerolic acid, and analogs thereof

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- Number: US 11,306,050 B2
- Document ID: US11306050B2
- Status: Granted
- Kind: B2
- Application number: 17/495,058
- Filed: 2021-10-06
- Published: 2022-01-27
- Granted: 2022-04-19
- Earliest claimed: 2020-05-12
- Assignees: Canopy Growth Corporation
- Applicants: Canopy Growth Corporation
- Inventors: Daniel Brumar; Mahmood Azizpour Fard; Ben Geiling; Mohammadmehdi Haghdoost Manjili
- Web page: https://patentgrep.com/patent/US11306050B2

## CPC

- C07C 37/16: by condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom
- B01J 21/04: Alumina
- B01J 21/16: Clays or other mineral silicates
- B01J 27/128: with iron group metals or platinum group metals
- B01J 31/0229: {also containing elements or functional groups covered by B01J31/0201 - B01J31/0214}
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

Disclosed are methods for preparing cannabigerol (CBG) or a CBG analog, embodiments of the method comprising providing a compound (I); combining the compound (I) with geraniol and a solvent to form a reaction mixture; and combining the reaction mixture with an acid catalyst to form a product mixture comprising the CBG or the CBG homolog. The method may further comprise separating the CBG or the CBG analog from the product mixture and may further comprise purifying the CBG or CBG analog. Methods for preparing cannabigerolic acid (CBGA) or a cannabigerolic acid analog are also disclosed. The present disclosure also provides highly purity CBG, CBGA, and analogs thereof.

## Claims

### Claim 1

A method for preparing cannabigerol (CBG) or a CBG analog, comprising:
reacting geraniol with a compound (I) of the following structure:
wherein R1 is hydrogen, C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl, (OCH2CH2)0-6O(C1-C8 alkyl), (C0-C4 alkyl)-NR2aR2b, (C0-C4 alkyl)-aryl, (C0-C4 alkyl)-heteroaryl, (C0-C4 alkyl)-cycloalkyl, or (C0-C4 alkyl)-heterocycloalkyl, wherein R2a and R2b are each independently hydrogen or C1-C6 alkyl;
in the presence of acidic alumina and optionally a solvent.

### Claim 2 (depends on 1)

The method of claim 1, wherein the method includes the solvent.

### Claim 3 (depends on 2)

The method of claim 2, wherein the solvent is chloroform, heptane, tert-butylmethyl ether, diethyl ether, dichloromethane, dichloroethane, trifluorotoluene, hexane, cyclohexane, pentane, toluene, or any combination thereof.

### Claim 4 (depends on 1)

The method of claim 1, wherein the compound (I) and geraniol are present in a compound (I):geraniol molar ratio of between about 1:1.5 and about 1:3.5.

### Claim 5 (depends on 1)

The method of claim 1, wherein R1 is C1-C12 alkyl.

### Claim 6 (depends on 1)

The method of claim 1, wherein R1 is C5H11.

### Claim 7 (depends on 1)

The method of claim 1, wherein R1 is C3H7.

### Claim 8 (depends on 1)

The method of claim 1, wherein R1 is C7H15.

### Claim 9 (depends on 1)

The method of claim 1, wherein the compound (I) and geraniol are present in a compound (I):geraniol molar ratio of between about 10:1 and about 1:10.

### Claim 10 (depends on 1)

The method of claim 1, wherein the compound (I) and geraniol are present in a compound (I):geraniol molar ratio of between 10:1 and 1:1.

### Claim 11 (depends on 1)

The method of claim 1, wherein the acid alumina is in an amount of between about 0.001 and about 10 molar equivalents with respect to the compound (I).

### Claim 12 (depends on 1)

The method of claim 1, wherein the acid alumina is in an amount of between about 0.001 and about 1 molar equivalents with respect to the compound (I).

### Claim 13 (depends on 1)

The method of claim 1, wherein the reacting step is performed with heating.

### Claim 14

A method for preparing cannabigerol (CBG) or a CBG analog, comprising:
reacting geraniol with a compound (I) of the following structure:
wherein R1 is C1-C12 alkyl;
in the presence of acidic alumina an acid catalyst and a solvent.

### Claim 15 (depends on 14)

The method of claim 14, wherein the solvent is chloroform, heptane, tert-butylmethyl ether, diethyl ether, dichloromethane, dichloroethane, trifluorotoluene, hexane, cyclohexane, pentane, toluene, or any combination thereof.

### Claim 16 (depends on 14)

The method of claim 14, wherein the compound (I) and geraniol are present in a compound (I):geraniol molar ratio of between about 10:1 and about 1:10.

### Claim 17 (depends on 14)

The method of claim 14, wherein the reacting step is performed with heating.

### Claim 18

A method for preparing cannabigerol (CBG) or a CBG analog, comprising:
reacting geraniol with a compound (I) of the following structure:
wherein R1 is hydrogen, C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl, (OCH2CH2)0-6O(C1-C8 alkyl), (C0-C4 alkyl)-NR2aR2b, (C0-C4 alkyl)-aryl, (C0-C4 alkyl)-heteroaryl, (C0-C4 alkyl)-cycloalkyl, or (C0-C4 alkyl)-heterocycloalkyl, wherein R2a and R2b are each independently hydrogen or C1-C6 alkyl;
under heating in the presence of acidic alumina and a solvent,
wherein the compound (I) and geraniol are present in a compound (I):geraniol molar ratio of between about 10:1 and about 1:10.

### Claim 19 (depends on 18)

The method of claim 18, wherein the solvent is chloroform, heptane, tert-butylmethyl ether, diethyl ether, dichloromethane, dichloroethane, trifluorotoluene, hexane, cyclohexane, pentane, toluene, or any combination thereof.

### Claim 20 (depends on 18)

The method of claim 18, wherein R1 is C1-C12 alkyl.