Various aspects of this disclosure relate to gas phase methods to decarboxylate cannabinoid carboxylic acids.

Various aspects of this disclosure relate to gas phase methods to decarboxylate cannabinoid carboxylic acids.

The present invention relates to intermediate compounds for the synthesis of novel cannabinoids 1 and 2, synthesized from simple starting materials using a cascade sequence of allylic rearrangement, aromatization and, for tetracyclic cannabinoids, further highly stereoselective and regioselective cyclization. These synthesized cannabinoids can more easily be obtained at high purity levels than cannabinoids isolated or synthesized via known methods. The cannabinoids 2 are obtained containing very low levels of isomeric cannabinoids such as the undesirable Δ.sup.8-tetrahydrocannabinol. The analogues with variation in aromatic ring substituents, whilst easily synthesized with the new methodology, would be much more difficult to make from any of the components of cannabis oil. ##STR00001##
Novel compounds of the formulas 3 and 6, useful as intermediates for the synthesis of the cannabinoids of advanced intermediates 4 and 5 as well as cannabinoids of the formulas 1 and 2, are disclosed. ##STR00002##

The present invention relates to intermediate compounds for the synthesis of novel cannabinoids 1 and 2, synthesized from simple starting materials using a cascade sequence of allylic rearrangement, aromatization and, for tetracyclic cannabinoids, further highly stereoselective and regioselective cyclization. These synthesized cannabinoids can more easily be obtained at high purity levels than cannabinoids isolated or synthesized via known methods. The cannabinoids 2 are obtained containing very low levels of isomeric cannabinoids such as the undesirable Δ.sup.8-tetrahydrocannabinol. The analogues with variation in aromatic ring substituents, whilst easily synthesized with the new methodology, would be much more difficult to make from any of the components of cannabis oil. ##STR00001##
Novel compounds of the formulas 3 and 6, useful as intermediates for the synthesis of the cannabinoids of advanced intermediates 4 and 5 as well as cannabinoids of the formulas 1 and 2, are disclosed. ##STR00002##

The present invention relates to intermediate compounds for the synthesis of novel cannabinoids 1 and 2, synthesized from simple starting materials using a cascade sequence of allylic rearrangement, aromatization and, for tetracyclic cannabinoids, further highly stereoselective and regioselective cyclization. These synthesized cannabinoids can more easily be obtained at high purity levels than cannabinoids isolated or synthesized via known methods. The cannabinoids 2 are obtained containing very low levels of isomeric cannabinoids such as the undesirable Δ.sup.8-tetrahydrocannabinol. The analogues with variation in aromatic ring substituents, whilst easily synthesized with the new methodology, would be much more difficult to make from any of the components of cannabis oil. ##STR00001##
Novel compounds of the formulas 3 and 6, useful as intermediates for the synthesis of the cannabinoids of advanced intermediates 4 and 5 as well as cannabinoids of the formulas 1 and 2, are disclosed. ##STR00002##

A series of new macrocycles and cage-like molecules are obtained in a high yield from a bis-(2,4-dialkoxyphenyl)arene (naphthalene, anthracene, pyrene, porphyrin, etc.) or a tris-(2,4-dialkoxyphenyl)arene (benzene, sym-tribenzobenzene) and paraformaldehyde under the catalysis of a Lewis acid. In addition, perhydroxybiphenylarenes (tetrabiphenyl trimer, naphthalene dimer, etc.) can be obtained by means of demethylation, and a variety of water-soluble derivatives can be obtained by further modification, with same exhibiting a good bond ability for guest molecules (purpurine, etc.). Moreover, the functional group introduced into the backbone enables the macrocycle to have excellent adsorption and separation capabilities and a photophysical property. The macrocyclic and cage-like molecules have commercially available raw materials, are simple to synthesize, have a high yield, and are convenient to modify, such that same have wide application prospects in gas adsorption and separation, facilitate performance improvement of luminescent materials, perform adsorption of water-soluble toxic substances, etc.

A series of new macrocycles and cage-like molecules are obtained in a high yield from a bis-(2,4-dialkoxyphenyl)arene (naphthalene, anthracene, pyrene, porphyrin, etc.) or a tris-(2,4-dialkoxyphenyl)arene (benzene, sym-tribenzobenzene) and paraformaldehyde under the catalysis of a Lewis acid. In addition, perhydroxybiphenylarenes (tetrabiphenyl trimer, naphthalene dimer, etc.) can be obtained by means of demethylation, and a variety of water-soluble derivatives can be obtained by further modification, with same exhibiting a good bond ability for guest molecules (purpurine, etc.). Moreover, the functional group introduced into the backbone enables the macrocycle to have excellent adsorption and separation capabilities and a photophysical property. The macrocyclic and cage-like molecules have commercially available raw materials, are simple to synthesize, have a high yield, and are convenient to modify, such that same have wide application prospects in gas adsorption and separation, facilitate performance improvement of luminescent materials, perform adsorption of water-soluble toxic substances, etc.

In this invention, a portion of the products from a pyrolysis reactor are reacted in a process to form one or more chemical intermediates.

In this invention, a portion of the products from a pyrolysis reactor are reacted in a process to form one or more chemical intermediates.

The present invention is directed to a method for preparing a final phenolic product from biomass comprising the steps of providing a furanic compound obtainable from biomass; reacting the furanic compound with a dienophile to obtain a phenolic compound; reacting the phenolic compound further to obtain the final phenolic product.