Method for the production of 6,12-dihydro-6-hydroxy-cannabidiol and the use thereof for the production of trans-delta-9-tetrahydrocannabinol

• US 5,227,537 A
• Filed: 01/08/1992
• Issued: 07/13/1993
• Est. Priority Date: 01/09/1991
• Status: Expired due to Fees

• Current Assignee: Heinrich Mack Nachf.
• Original Assignee: Heinrich Mack Nachf.
• Inventors: Stoss, Peter, Merrath, Peter
• Primary Examiner(s): Lone, Werren B.
• Application Number:
  US07/818,040
• Time in Patent Office: 552 Days
• Field of Search: 568/743, 568/808, 568/809, 568/811, 568/619, 568/620
• US Class Current: 568/811
• CPC Class Codes: C07C 2601/16 the ring being unsaturated
• CPC Class Codes: C07C 37/14 by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
• CPC Class Codes: C07C 39/17 containing other rings in addition to the six-membered aromatic rings , e.g. cyclohexylphenol
• CPC Class Codes: C07C 39/23 polycyclic, containing six-membered aromatic rings and other rings, with unsaturation outside the aromatic rings
• CPC Class Codes: C07D 311/80 Dibenzopyrans; Hydrogenated dibenzopyrans

Abstract

A method is described for the production of 6,12-dihydro-6-hydroxy-cannabidiol which is obtained by the reaction of olivetol and cis-p-menth-2-ene-1,8,-diol and the reaction thereof to yield trans-delta-9-tetrahydrocannabinol.

Claims

1. A method of producing 6,12-dihydrohydroxy-cannabidiol of the formula (I) ##STR2## wherein an equimolar amount of olivetol of the formula (II) ##STR3## is reacted with cis-p-menth-2-ene-1,8-diol of the formula (III) ##STR4## in an organic solvent in the presence of a Lewis acid catalyst.

2. The method as claimed in claim 1, wherein the solvent is selected from the group consisting essentially of aromatic hydrocarbons, halogenated hydrocarbons, ethers, and mixtures thereof.

3. The method as claimed in claim 2, wherein the solvent is selected from the group consisting essentially of toluene, benzene, methylene chloride and chloroform, and mixtures thereof.

4. The method as claimed in claim 1, wherein a protein acid, an organic sulfonic acid or another Lewis acid is used as a catalyst.

5. The method as claimed in claim 4, wherein the catalyst is hydrochloric acid or p-toluenesulfonic acid.

6. The method as claimed in claim 1, wherein the 6,12-dihydro-6-hydroxy-cannabidiol is further purified by crystallization from petroleum ether.

8. The method as claimed in claim 6, wherein said solvent is selected from the group consisting essentially of methylene chloride and chloroform.

9. The method as claimed in claim 1, wherein the catalyst is selected from the group consisting essentially of zinc chloride and zinc bromide.

12. The method as claimed in claim 2, wherein a protein acid, an organic sulfonic acid or another Lewis acid is used as a catalyst.

13. The method as claimed in claim 3, wherein a protein acid, an organic sulfonic acid or another Lewis acid is used as a catalyst.

14. The method as claimed in claim 2, wherein the 6,12-dihydro-6-hydroxy-cannabidiol is further purified by crystallization from petroleum ether.

15. The method as claimed in claim 3, wherein the 6,12-dihydro-6-hydroxy-cannabidiol is further purified by crystallization from petroleum ether.

16. The method as claimed in claim 4, wherein the 6,12-dihydro-6-hydroxy-cannabidiol is further purified by crystallization from petroleum ether.

17. A method according to claim 1, wherein the reaction product is further purified by crystallization.

7. A method for producing trans-delta-9-tetrahydrocannabidiol of the formula (IV) ##STR5## wherein a ring condensation is performed on 6,12-dihydro-6-hydroxy-cannabidiol of the formula (I) ##STR6## in a solvent selected from the group consisting essentially of hydrocarbons, aromatic hydrocarbons and chlorinated hydrocarbons and in the presence of a Lewis acid as a catalyst.

10. The method as claimed in claim 7, wherein the ring condensation is performed in the presence of a water binding substance.

11. The method as claimed in claim 10, wherein the water binding substance is a molecular sieve.