- SYNTHESIS OF PHYTOCANNABINOIDS INCLUDING A DECARBOXYLATION STEP
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method for decarboxylating a carboxylated phytocannabinoid compound of Formula I to form a phytocannabinoid compound of Formula II: Formula I Formula II wherein: R1 is selected from the group consisting of: substituted or unsubstituted C1-C5 alkyl; R2 is selected from the group consisting of: OH or O, and R3 is selected from the group consisting of: a substituted or unsubstituted cyclohexene, a substituted or unsubstituted C2-C8 alkene, or a substituted or unsubstituted C2-C8 dialkene; or R2 is O, and R2 and R3 together form a ring structure in which R2 is an internal ring atom; wherein the method includes heating a reaction mixture comprising the carboxylated phytocannabinoid compound and a polar aprotic solvent in the presence of a LiCl for a time sufficient to decarboxylate at least a portion of the carboxylated phytocannabinoid compounds and form the phytocannabinoid compound.
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Page/Page column 16
(2019/03/05)
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- SYNTHESIS OF PHYTOCANNABINOIDS INCLUDING A DEMETHYLATION STEP
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A method for demethylating a methylated phytocannabinoid compound of Formula I to form a phytocannabinoid compound of Formula II: Formula I Formula II wherein: R1 is selected from the group consisting of: substituted or unsubstituted C1-C5 alkyl; R2 is selected from the group consisting of: OH or O, and R3 is selected from the group consisting of: a substituted or unsubstituted cyclohexene, a substituted or unsubstituted C2-C8 alkene, or a substituted or unsubstituted C2-C8 dialkene; or R2 is O, and R2 and R3 together form a ring structure in which R2 is an internal ring atom; wherein the method includes: heating a reaction mixture comprising the methylated phytocannabinoid compounds and a polar aprotic solvent in the presence of a dissolved inorganic alkaline salt for a time sufficient to demethylate at least a portion of the methylated phytocannabinoid compounds and form the phytocannabinoid compound.
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Page/Page column 16-17
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- Chemistry of 1,3,5-Tris(trimethylsiloxy)-1-methoxyhexa-1,3,5-triene, a β-Tricarbonyl Trianion Equivalent
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The title compound has been synthesized and its chemistry studied.Condensation with orthoesters, acid chlorides, or imidazolides gave aromatic compounds in a 5C + 1C condensation.A formal synthesis of lasiodiplodin has been completed.
- Chan, T. H.,Stoessel, D.
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p. 2423 - 2428
(2007/10/02)
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- A BIOMIMETIC SYNTHESIS OF 1Δ-TETRAHYDROCANNABIOL
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Condensation of 1,3-bis(trimethylsiloxy)-1-methoxybutadiene with the acid chloride 12 gave methyl olivetolate (13).Condensation of 13 with (+)-p-mentha-2,8-dien-1-ol gave methyl 1Δ-tetrahydrocannabiolate (14) in 55percent isolated yield.Alkaline hydrolysis of 14 gave 1Δ-tetrahydrocannabinol (1, 1Δ-THC).The synthesis is patterned after the biogenesis of 1.
- Chan, T. H.,Chaly, T.
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p. 2935 - 2938
(2007/10/02)
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- Convenient Syntheses of Alkyl β-Resorcylate Derivatives
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Syntheses of methyl 2,4-dihydroxy-6-methyl- (1a) and -3,6-dimethylbenzoates (1b) and methyl 2,4-dihydroxy-6-pentylbenzoate (1c) are described.Condensation reactions of dimethyl sodiomalonate with the dianion derived from pentane-2,4-dione or the dimerisation of the methyl acetoacetate dianion or the acetylation of the trianion derived from methyl 3,5,7-trioxo-octanoate gave (1a) (78percent) after work-up at pH 9.Analogous convenient, short, optimised syntheses of (1b and c) are given in detail.
- Barrett, Anthony G. M.,Morris, Timothy M.,Barton, Derek H. R.
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p. 2272 - 2277
(2007/10/02)
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