Methods of synthesizing cannabigerol, cannabigerolic acid, and analogs thereof

A method for preparing cannabigerolic acid (CBGA) or a CBGA analog, the method comprising:

• reacting geraniol with a compound (II) of the following structure:
• wherein R1 is hydrogen, C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl, (OCH2CH2)0-6O(C1-C8 alkyl), (C0-C4 alkyl)-NR2aR2b (C0-C4 alkyl)-aryl, (C0-C4 alkyl)-heteroaryl, (C0-C4 alkyl)-cycloalkyl, or (C0-C4 alkyl)-heterocycloalkyl, wherein R2a and R2b are each independently hydrogen or C1-C6 alkyl;
• in the presence of an acid catalyst and optionally a solvent, wherein the acid catalyst is camphorsulfonic acid, acidic alumina, montmorillonite K10, iron (III) perchlorate hydrate, or a combination thereof;
• and
• hydrolyzing with one or more mild hydrolysis reagents to provide the CBGA or CBGA analog.

A method for preparing cannabigerolic acid (CBGA) or a CBGA analog, the method comprising:

• reacting geraniol with a compound (II) of the following structure:
• wherein R1 is hydrogen, C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl, (OCH2CH2)0-6O(C1-C8 alkyl), (C0-C4 alkyl)-NR2aR2b, (C0-C4 alkyl)-aryl, (C0-C4 alkyl)-heteroaryl, (C0-C4 alkyl)-cycloalkyl, or (C0-C4 alkyl)-heterocycloalkyl, wherein R2a and R2b are each independently hydrogen or C1-C6 alkyl;
• in the presence of acidic alumina and a solvent, wherein the compound (II) and geraniol are present in a compound (II):geraniol molar ratio of between 10:1 and 1:10;
• and
• hydrolyzing with one or more mild hydrolysis reagents to provide the CBGA or CBGA analog.