The present invention provides a method for preparing ingenol-3-angelate.

A process of dissolving

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in a solvent to produce a first mixture. To the first mixture a reagent is added to produce a second mixture. A HRR is then added to the second mixture to produce a third mixture. The third mixture is then refluxed to produce

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A process of dissolving

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in a solvent to produce a first mixture. To the first mixture a reagent is added to produce a second mixture. A HRR is then added to the second mixture to produce a third mixture. The third mixture is then refluxed to produce

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Fatty acids are produced through transacylation. An organic nitrogen-containing compound is reacted with alkyl sultone to generate a white solid of a zwitterionic compound. After being purified and dried, the white solid is powdered to be reacted with a Bronsted strong acid for obtaining a clear viscous water-based acidic ionic liquid (IL) as a catalyst used used to effectively process transacylation between oil and acetic acid (HOAc) for fabricating fatty acid (FFA) and glycerol triacetate (GTA). Therein, unsaturated fatty acid is simultaneously processed through addition acetoxylation to obtain stabilized acetoxy fatty acid (AFFA). After, HOAc is recycled through vacuuming. Then, the product and the IL are stratified. The product at upper layer is taken out. The IL at lower layer can be recycled for processing transacylation and addition acetoxylation repeatedly. Therein, fatty acids including the stabilized AFFA are obtained from the product after taking out GTA through vacuum distillation.

Methods are provided for the synthesis of cannabinoids, including cannabidiol (CBD), cannabinol (CBN), cannabichromene (CBC), cannabidiolic acid (CBDA), cannabigerol (CBG), cannabigerolic acid (CBGA), cannabidivarin (CBDV), cannabidibutol (CBD-C4), dihydrocannabidiol (DCBD), tetrahydrocannabivarin (THCV), analogs thereof, and precursors to the foregoing. One method employs phloroglucinol or a phloroglucinol analog as a starting material. The syntheses are stereospecific, efficient, selective, and cost-effective, with little or no potential for generation of THC (()-trans-.sup.9-tetrahydro-cannabinol) or any other psychoactive side product. Telescoped syntheses are also provided, as are new cannabinoids, pharmaceutical formulations, and methods of use.

Methods are provided for the synthesis of cannabinoids, including cannabidiol (CBD), cannabinol (CBN), cannabichromene (CBC), cannabidiolic acid (CBDA), cannabigerol (CBG), cannabigerolic acid (CBGA), cannabidivarin (CBDV), cannabidibutol (CBD-C4), dihydrocannabidiol (DCBD), tetrahydrocannabivarin (THCV), analogs thereof, and precursors to the foregoing. One method employs phloroglucinol or a phloroglucinol analog as a starting material. The syntheses are stereospecific, efficient, selective, and cost-effective, with little or no potential for generation of THC (()-trans-.sup.9-tetrahydro-cannabinol) or any other psychoactive side product. Telescoped syntheses are also provided, as are new cannabinoids, pharmaceutical formulations, and methods of use.

The present invention provides an 8-(acyloxy)alkanal compound (1), wherein n represents 0 or 1, and R.sup.1 represents a linear or branched alkyl group having 1 to 10 carbon atoms, a phenyl group, or a phenyl group in which one or more hydrogen atoms are substituted with a halogen atom, and a process for preparing the same. The process comprises the steps of subjecting the aforesaid 8-(acyloxy)alkanal compound (1) to a nucleophilic addition reaction with a nucleophilic reagent, alkyl compound (2), wherein M.sup.1 represents Li, MgZ.sup.1, CuZ.sup.1, or CuLiZ.sup.1, n represents 0 or 1, and Z.sup.1 represents a halogen atom, a methyl group, or an ethyl group, to form 2,9-undecanediol (3), and subjecting the 2,9-undecanediol (3) to an acetylation reaction to form the 2,9-diacetoxyundecane (4).

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The present invention provides an 8-(acyloxy)alkanal compound (1), wherein n represents 0 or 1, and R.sup.1 represents a linear or branched alkyl group having 1 to 10 carbon atoms, a phenyl group, or a phenyl group in which one or more hydrogen atoms are substituted with a halogen atom, and a process for preparing the same. The process comprises the steps of subjecting the aforesaid 8-(acyloxy)alkanal compound (1) to a nucleophilic addition reaction with a nucleophilic reagent, alkyl compound (2), wherein M.sup.1 represents Li, MgZ.sup.1, CuZ.sup.1, or CuLiZ.sup.1, n represents 0 or 1, and Z.sup.1 represents a halogen atom, a methyl group, or an ethyl group, to form 2,9-undecanediol (3), and subjecting the 2,9-undecanediol (3) to an acetylation reaction to form the 2,9-diacetoxyundecane (4).

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4-Aralkylphenols and derivatives thereof expressed by general formulas (6) and (7) are useful for producing trisphenols. ##STR00001##

4-Aralkylphenols and derivatives thereof expressed by general formulas (6) and (7) are useful for producing trisphenols. ##STR00001##