Process for the production of cannabidiol and delta-9-tetrahydrocannabinol

Abstract

The present disclosure relates to the preparation of a cannabidiol compound or a derivative thereof. The cannabidiol compound or derivatives thereof can be prepared by an acid-catalyzed reaction of a suitably selected and substituted di-halo-olivetol or derivative thereof with a suitably selected and substituted cyclic alkene to produce a dihalo-cannabidiol compound or derivative thereof. The dihalo-cannabidiol compound or derivative thereof can be produced in high yield, high stereospecificity, or both. It can then be converted under reducing conditions to a cannabidiol compound or derivatives thereof.

We claim: 
     
         1 .- 20 . (canceled) 
     
     
         21 . A composition comprising a compound of formula (XVI): 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof, 
         wherein said composition comprises at least 99.96 area % of the compound of formula (XVI) and less than 0.04 area % of 4,6-dihalo-5-pentylbenzene-1,3-diol, 4-halo-5-pentylbenzene-1,3-diol, 6-halo-5-pentylbenzene-1,3-diol, and delta-9-tetrahydrocannabinol. 
       
     
     
         22 . The composition of  claim 21 , wherein said composition is a white crystalline powder. 
     
     
         23 . The composition of  claim 21 , wherein said halo is chloro or bromo. 
     
     
         24 . The composition of  claim 23 , wherein said halo is bromo. 
     
     
         25 . The composition of  claim 24 , comprising a compound of formula (XVI): 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof, 
         wherein said composition comprises at least 99.96 area % of the compound of formula (XVI) and less than 0.04 area % of 4-bromo-5-pentylbenzene-1,3-diol, 6-bromo-5-pentylbenzene-1,3-diol, and delta-9-tetrahydrocannabinol. 
       
     
     
         26 . The composition of  claim 21 , wherein said compound of formula (XVI) has an enantiomeric excess of at least about 99%. 
     
     
         27 . A composition comprising a compound of formula (XVI): 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof; 
         wherein said composition comprises no more than 400 ppm of 4,6-dihalo-5-pentylbenzene-1,3-diol, 4-halo-5-pentylbenzene-1,3-diol, 6-halo-5-pentylbenzene-1,3-diol, and delta-9-tetrahydrocannabinol. 
       
     
     
         28 . The composition of  claim 27 , wherein said halo is chloro or bromo. 
     
     
         29 . The composition of  claim 28 , wherein said halo is bromo. 
     
     
         30 . The composition of  claim 29 , comprising no more than 400 ppm of 4-bromo-5-pentylbenzene-1,3-diol, 6-bromo-5-pentylbenzene-1,3-diol, and delta-9-tetrahydrocannabinol 
     
     
         31 . The composition of  claim 27 , wherein said composition is a white crystalline powder. 
     
     
         32 . The composition of  claim 27 , wherein said compound of formula (XVI) has an enantiomeric excess of at least about 99%.