Novel synthesis of (−)‐ trans ‐Δ 9,11 ‐tetrahydrocannabinol | Zendy

Banijamali Ali R. | Zendy; Makriyannis Alexandros | Zendy

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Novel synthesis of (−)‐ trans ‐Δ 9,11 ‐tetrahydrocannabinol

Author(s) -

Banijamali Ali R.,

Makriyannis Alexandros

Publication year - 1988

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570250324

Subject(s) - chemistry , dichloromethane , anhydrous , hydrogen chloride , chloride , yield (engineering) , zinc , potassium , medicinal chemistry , hydrogen , nuclear chemistry , inorganic chemistry , organic chemistry , chromatography , solvent , materials science , metallurgy

Addition of hydrogen chloride gas to a solution of Δ 8 ‐tetrahydrocannabinol in dry dichloromethane at ‐60° in the presence of zinc chloride results in the formation of a higher concentration of 9‐α‐chlorohexa‐hydrocannabinol (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‐chlorohexa‐hydrocannabinol using potassium t ‐amylate under anhydrous conditions gives exclusively Δ 9,11 ‐tetrahydrocannabinol in overall yield of 65%.

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