Journal of Heterocyclic Chemistry p. 823 - 825 (1988)
Update date:2022-08-05
Topics:
Banijamali
Makriyannis
Addition of hydrogen chloride gas to a solution of Δ8-tetrahydrocannabinol in dry dichloromethane at -60° in the presence of zinc chloride results in the formation of a higher concentration of 9-α-chlorohexahydrocannabinol (75%) than the thermodynamically more stable 9-β-chlorohexahydrocannabinol (25%). The two isomers can be separated by reverse-phase hplc. Elimination of hydrogen chloride from 9-α-chlorohexahydrocannabinol using potassium t-amylate under anhydrous conditions gives exclusively Δ9,11-tetrahydrocannabinol in overall yield of 65%.
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