Patent classifications
C07C37/56
Synthetic intermediates for novel cannabinoids and cannabinoid acids and their derivatives
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##
Synthetic intermediates for novel cannabinoids and cannabinoid acids and their derivatives
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##
Cannabis thin layer decarboxylation
Dried and or decarboxylated cannabis containing a known composition of cannabinoids is blended with other dried or decarboxylated cannabis of a known composition of cannabinoids and or mixed with other extracts of, isolates of, cannabisor synthetic cannabinoids to achieve a prescribed amount of cannabinoids in the blend. Decarboxylated cannabis is preferentially produced using controlled thin layer decarboxylation. Precision decarboxylation is optionally used to produce a precise pair ratio of acidic to neutral cannabinoid, eg THCA to THC or CBDA to CBD. Further a prescribed or selected terpene profile is mixed and applied to the blend. Once mixed the plant material is suitable for ingestion without further treatment and is dosed appropriately.
Cannabis thin layer decarboxylation
Dried and or decarboxylated cannabis containing a known composition of cannabinoids is blended with other dried or decarboxylated cannabis of a known composition of cannabinoids and or mixed with other extracts of, isolates of, cannabisor synthetic cannabinoids to achieve a prescribed amount of cannabinoids in the blend. Decarboxylated cannabis is preferentially produced using controlled thin layer decarboxylation. Precision decarboxylation is optionally used to produce a precise pair ratio of acidic to neutral cannabinoid, eg THCA to THC or CBDA to CBD. Further a prescribed or selected terpene profile is mixed and applied to the blend. Once mixed the plant material is suitable for ingestion without further treatment and is dosed appropriately.
MICROWAVE-ASSISTED DECARBOXYLATION OF ORGANIC ACIDS IN HEMP MATERIALS
The present disclosure provides a method for decarboxylation of organic acids in hemp materials. The method includes placing hemp biomass in a container. The method further includes heating the hemp biomass using a microwave so that the hemp biomass receives between 100 J/g and 2,000 J/g, inclusive, total microwave energy. The method further includes decarboxylating the hemp biomass to form decarboxylated products.
MICROWAVE-ASSISTED DECARBOXYLATION OF ORGANIC ACIDS IN HEMP MATERIALS
The present disclosure provides a method for decarboxylation of organic acids in hemp materials. The method includes placing hemp biomass in a container. The method further includes heating the hemp biomass using a microwave so that the hemp biomass receives between 100 J/g and 2,000 J/g, inclusive, total microwave energy. The method further includes decarboxylating the hemp biomass to form decarboxylated products.
Cannabinoids and cannabinoid acids and their derivatives
The present invention relates to 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 Δ8-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. Novel compounds of the formulas 3, 4, 5 and 6, as intermediates for the synthesis of the cannabinoids of the formulas 1 and 2 are also disclosed.
Cannabinoids and cannabinoid acids and their derivatives
The present invention relates to 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 Δ8-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. Novel compounds of the formulas 3, 4, 5 and 6, as intermediates for the synthesis of the cannabinoids of the formulas 1 and 2 are also disclosed.
HIGH PURITY 4-HYDROXYSTYRENE SOLUTION, METHOD OF PRODUCING THE SAME, AND METHOD OF PRODUCING 4-HYDROXYSTYRENE POLYMER
Provided are a 4-hydroxystyrene solution with high purity and good storage stability that is suitable as a source for producing a 4-hydroxystyrene polymer on a commercial scale, and a method of producing the solution. The method of producing a 4-hydroxystyrene solution of the present invention includes the following steps (i) to (iv): (i) deprotection step for contacting 4-acetoxystyrene with a base in a solvent to produce 4-hydroxystyrene; (ii) neutralization step for adding an acid to the solution containing 4-hydroxystyrene after deprotection to neutralize the solution; (iii) step for washing the solution containing 4-hydroxystyrene after neutralization with water; and (iv) solvent replacement step for adding a solvent that can dissolve 4-hydroxystyrene to the solution containing 4-hydroxystyrene followed by distillation at 40° C. or lower to remove other components than 4-hydroxystyrene and excess solvent.
HIGH PURITY 4-HYDROXYSTYRENE SOLUTION, METHOD OF PRODUCING THE SAME, AND METHOD OF PRODUCING 4-HYDROXYSTYRENE POLYMER
Provided are a 4-hydroxystyrene solution with high purity and good storage stability that is suitable as a source for producing a 4-hydroxystyrene polymer on a commercial scale, and a method of producing the solution. The method of producing a 4-hydroxystyrene solution of the present invention includes the following steps (i) to (iv): (i) deprotection step for contacting 4-acetoxystyrene with a base in a solvent to produce 4-hydroxystyrene; (ii) neutralization step for adding an acid to the solution containing 4-hydroxystyrene after deprotection to neutralize the solution; (iii) step for washing the solution containing 4-hydroxystyrene after neutralization with water; and (iv) solvent replacement step for adding a solvent that can dissolve 4-hydroxystyrene to the solution containing 4-hydroxystyrene followed by distillation at 40° C. or lower to remove other components than 4-hydroxystyrene and excess solvent.