Methods of preparing synthetic cannabichromene and cannabicitran and derivatives thereof

A method of preparing a compound of Formula I or II,

• wherein,
• R1 is selected from the group consisting of hydroxyl and C1-5alkoxy;
• R2 and R4 are in each instance independently selected from the group consisting of hydrogen, —C1-5alkyl, —CF3, cyano, nitro, phenyl, —C(O)R6, —NRaRb, —C(O)OR6, —O—C(O)R6, —O—R6, —O—R6, —C(H)═C(R6)2, —N(H)C(O)R6, halo, —N(R6)3;
• wherein, Ra and Rb are each independently hydrogen or C1-5alkyl;
• wherein, R6 is hydrogen or C1-5alkyl;
• R3 is selected from the group consisting of hydrogen, linear or branched C1-10alkyl;
• R5 is selected from the group consisting of hydrogen, C1-5alkyl, C1-5alkenyl and prenyl;
• comprising:
• dosing at a first temperature above 65° C. a compound of Formula Ia
• wherein, R5 is as described above;
• to a first mixture, said first mixture comprising an amine and a compound of Formula Ib
• wherein,
• R1a is selected from the group consisting of hydroxyl and C1-5alkoxy;
• R2a and R4a are each as described above for R2 and R4;
• R3a is selected from the group consisting of hydrogen, linear or branched C1-10alkyl;
• and
• R7 is selected from the group consisting of hydrogen, —C(O)Rc,
• wherein Rc is hydrogen or C1-5alkyl;
• to form a second mixture;
• and,
• allowing the second mixture to react at a second temperature;
• wherein, a compound of Formula I or II is prepared.