Synthesis of Neocannabinoids Using Controlled Friedel-Crafts Reactions

09 June 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


A simple, one-step transformation to produce 8,9-dihydrocannabidiol (H2CBD) and related “neocannabinoids” via controlled Friedel-Crafts reactions is reported. Experimental and computational studies probing the mechanism of neocannabinoid synthesis from cyclic allylic alcohol and substituted resorcinol reaction partners provide understanding of the kinetic and thermody-namic factors driving regioselectivity for the reaction. Herein, we present a reaction scope for neocannabinoid synthesis including the production of both normal and abnormal isomers under both kinetic and thermodynamic control. Discovery and optimization of this one-step protocol between various allylic alcohols and resorcinol derivatives is discussed and supported with density-functional theory (DFT) calculations.



Supplementary materials

Supporting information
Complete Experimental and Analytical Data


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