IP Library › Granted Patent US 12,398,113
Granted Patent B2
US 12,398,113 · App. 17/644,690 · Granted Aug 26, 2025

Methods for converting CBD, CBDA and analogs thereof into Δ

Inventors: Christopher Adair (Smiths Falls, CA); Roger Gallant (Smiths Falls, CA); Ben Geiling (Smiths Falls, CA); Mohammadmehdi Haghdoost Manjili (Smiths Falls, CA)
Assignee: Canopy Growth Corporation
C07D311/78B01J29/40C07D311/80
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Quick Facts
Patent No.
US 12,398,113
App. No.
17/644,690
Granted
Aug 26, 2025
Kind
B2
Abstract

Disclosed herein are methods for converting cannabidiol, cannabidiolic acid and analogs thereof into Δ 8 -tetrahydrocannabinol, Δ 8 -tetrahydrocannabinolic acid and analogs thereof. In particular, there is provided a method for converting a compound of Formula (I) as defined herein into a compound of Formula (II) as defined herein, the method comprising heating the compound of Formula (I) and a Lewis acidic heterogeneous reagent in an aprotic-solvent system to provide a compound of Formula (II), wherein the Lewis-acidic heterogeneous reagent is acidic alumina.

Claims (25)

1. A method for converting a compound of Formula (I) into a compound of Formula (II), the method comprising heating a compound of Formula (I)

and a Lewis-acidic heterogeneous reagent in an aprotic-solvent system, to provide a compound of Formula (II)

wherein the Lewis-acidic heterogeneous reagent is acidic alumina, and

wherein:

R 1 is hydrogen or COOH, and

R 2 is hydrogen, C 1 -C 12 alkyl, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, (OCH 2 CH 2 ) 0-6 O(C 1 -C 8 alkyl), (C 0 -C 4 alkyl)-NR 2a R 2b , (C 0 -C 4 alkyl)-aryl, (C 0 -C 4 alkyl)-heteroaryl, (C 0 -C 4 alkyl)-cycloalkyl, or (C 0 -C 4 alkyl)-heterocycloalkyl, wherein R 2a and R 2b are each independently hydrogen or C 1 -C 6 alkyl.

2. The method of claim 1 , wherein the heating step occurs at a temperature in a range from about 80° C. to about 110° C.

3. The method of claim 1 , wherein the heating step occurs at a temperature in a range from about 80° C. to about 100° C.

4. The method of claim 1 , wherein the heating step occurs at a temperature in a range from about 80° C. to about 95° C.

5. The method of claim 1 , wherein the heating step occurs in an inert atmosphere.

6. The method of claim 1 , wherein the heating step is performed in a stirred tank reactor or a rotary bed reactor.

7. The method of claim 1 , wherein the Lewis-acidic heterogeneous reagent is in an amount of between about 0.1 to about 100 molar equivalents with respect to the compound of Formula (I).

8. The method of claim 1 , wherein the Lewis-acidic heterogeneous reagent is in an amount of between about 1 to about 50 molar equivalents with respect to the compound of Formula (I).

9. The method of claim 1 , wherein the Lewis-acidic heterogeneous reagent is in an amount of between about 1 to about 25 molar equivalents with respect to the compound of Formula (I).

10. The method of claim 1 , wherein the Lewis-acidic heterogeneous reagent is in an amount of between about 1 to about 10 molar equivalents with respect to the compound of Formula (I).

11. The method of claim 1 , wherein the Lewis-acidic heterogeneous reagent is in an amount of between about 1 to about 5 molar equivalents with respect to the compound of Formula (I).

12. The method of claim 1 , wherein the aprotic-solvent system comprises acetone, dimethyl sulfoxide, ethyl acetate, dichloromethane, chloroform, toluene, pentane, heptane, hexane, diethyl ether, tert-butyl methyl ether, tetrahydrofuran, dioxane, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, anisole, butyl acetate, cumene, ethyl formate, isobutyl acetate, isopropyl acetate, methyl acetate, methylethylketone, methylisobutylketone, propyl acetate, cyclohexane, para-xylene, meta-xylene, ortho-xylene, or 1,2-dichloroethane, or any combination thereof.

13. The method of claim 1 , wherein the aprotic-solvent system is heptane.

14. The method of claim 1 , further comprising drying the acidic alumina before the heating step.

15. The method of claim 1 , wherein R 1 is hydrogen.

16. The method of claim 1 , wherein R 2 is C 3 H 7 , C 5 H 11 or C 7 H 15 .

17. The method of claim 1 , wherein the compound of Formula (I) is cannabidiol (CBD) and the compound of Formula (II) is Δ 8 -tetrahydrocannabinol (Δ 8 -THC).

18. A method for converting cannabidiol (CBD) into Δ 8 -tetrahydrocannabinol (Δ 8 -THC), the method comprising heating CBD and a Lewis-acidic heterogeneous reagent in an aprotic-solvent system at a temperature in a range from about 80° C. to about 110° C., and wherein the Lewis-acidic heterogeneous reagent is acidic alumina and is in an amount of between about 1 to about 100 molar equivalents with respect to CBD.

19. The method of claim 18 , wherein the aprotic-solvent system comprises acetone, dimethyl sulfoxide, ethyl acetate, dichloromethane, chloroform, toluene, pentane, heptane, hexane, diethyl ether, tert-butyl methyl ether, tetrahydrofuran, dioxane, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, anisole, butyl acetate, cumene, ethyl formate, isobutyl acetate, isopropyl acetate, methyl acetate, methylethylketone, methylisobutylketone, propyl acetate, cyclohexane, para-xylene, meta-xylene, ortho-xylene, or 1,2-dichloroethane, or any combination thereof.

20. The method of claim 18 , wherein the aprotic-solvent system is heptane.

Assignments (4)
SECURITY INTEREST Recorded Jan 20, 2026
From: CANOPY GROWTH CORPORATION; TWEED INC.
To: JGB COLLATERAL LLC
Reel/Frame 073521/0250 →
RELEASE OF SECURITY INTEREST IN PATENT INTELLECTUAL PROPERTY Recorded Jan 9, 2026
From: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
To: CANOPY GROWTH CORPORATION
Reel/Frame 074281/0925 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 18, 2025
From: ADAIR, CHRISTOPHER; GEILING, BEN; HAGHDOOST MANJILI, MOHAMMADMEHDI
To: CANOPY GROWTH CORPORATION
Reel/Frame 071759/0582 →
NOTICE OF GRANT OF SECURITY INTEREST IN PATENTS Recorded Oct 16, 2023
From: CANOPY GROWTH CORPORATION
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 065239/0156 →
Continuity (3)
Continuation In Part 17596364
Provisional Application 62860097 · Jun 11, 2019
Related Publication 20220106283A1 · Apr 7, 2022
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