DIRECT SYNTHESIS OF (-)-TRANS-.DELTA. TETRAHYDROCANNABINOL FROM OLIVETOL AND (+)-TRANS-.DELTA. -CARENE OXIDE

• US 3,734,930 A
• Filed: 09/22/1971
• Issued: 05/22/1973
• Est. Priority Date: 09/22/1971
• Status: Expired due to Term

• Current Assignee: Handrick G. Richard, Raj Kumar Razdan
• Original Assignee: Handrick G. Richard, Raj Kumar Razdan
• Inventors: Razdan, Raj Kumar, Handrick, G. Richard
• Primary Examiner(s): Ford, John M.
• Application Number:
  US05/182,841
• Time in Patent Office: 608 Days
• Field of Search: 260/345.3
• US Class Current: 549/390
• CPC Class Codes: C07D 311/80 Dibenzopyrans; Hydrogenated dibenzopyrans

Abstract

A one step stereospecific synthesis of Delta 9tetrahydrocannabinol by the condensation of olivetol with Delta 2-carene oxide is disclosed.

Claims

2. A method as defined in claim 1, wherein said condensation is performed in the presence of an acid catalyst.

3. A method as defined in claim 1, wherein said catalyst is selected from the group consisting of boron trifluoride and p-toluenesulfonic acid.

4. A method as defined in claim 3, wherein said Delta 2-carene oxide and said olivetol are present in a molar ratio of 1.6:

1 and said catalyst is p-toluenesulfonic acid.

5. A method as defined in claim 3, wherein said Delta 2-cArene oxide and said olivetol are present in equimolar amounts.

6. A method as defined in claim 1, further comprising separating said Delta 9-tetrahydrocannabinol into trans- Delta 9-tetrahydrocannabinol and cis- Delta 9-tetrahydrocannabinol.

7. A method as defined in claim 6, wherein said trans- and cis-Delta 9-tetrahydrocannabinol are separated by vapor phase chromatography.