METHODS FOR CONVERTING TETRAHYDROCANNABINOLIC ACID INTO CANNABINOLIC ACID

1 . A method for converting tetrahydrocannabinolic acid (THCA) to cannabinolic acid (CBNA), the method comprising contacting an input material comprising the THCA with a benzoquinone reagent.

2 . (canceled)

3 . The method of claim 1 , wherein the input material is derived from marijuana biomass.

4 . The method of claim 1 , wherein the input material is a cannabis distillate, a cannabis resin, a cannabis extract, or a combination thereof.

5 . The method of claim 1 , wherein the input material is THCA in an isolated form.

6 . The method of claim 1 , wherein at least about 60 weight % of the THCA is Δ 9 -THCA.

7 . The method of claim 6 , wherein at least about 95 weight % of the THCA is Δ 9 -THCA.

8 . (canceled)

14 . The method of claim 1 , wherein the benzoquinone reagent comprises a compound as defined in formula (I) or formula (II):

wherein X 1 , X 2 , X 3 , and X 4 are each independently: H; a halide; a C <12 -hydrocarbyl; a C <12 -heteroaryl; a C <12 -heteroaralkyl; a C <12 -heteroaralkenyl; hydroxyl; a C <12 -alkoxy; a C <12 -amino; a C <12 -acyl; a C <12 -amide; a C <12 -ester; a C <12 -ketone; or a substituted analog thereof.

15 . The method of claim 1 , wherein the benzoquinone reagent comprises:

or a combination thereof.

16 . (canceled)

17 . (canceled)

18 . The method of claim 1 , wherein the contacting of the input material with the benzoquinone reagent is at a benzoquinone:THCA ratio of between about 1.0:1.0 and about 10.0:1.0 on a molar basis.

19 . The method of claim 18 , wherein the benzoquinone:THCA ratio is between about 2.0:1.0 and about 4.0:1.0 on a molar basis.

20 . The method of claim 1 , wherein the contacting of the input material with the benzoquinone reagent is at a temperature of between about 20° C. and about 190° C.

21 . The method of claim 1 , wherein the contacting of the input material with the benzoquinone reagent is at a temperature of between about 80° C. and about 110° C.

22 . (canceled)

23 . (canceled)

24 . The method of claim 1 , wherein the contacting of the input material with the benzoquinone reagent is in the presence of a solvent.

25 . The method of claim 24 , wherein the solvent is pentane, hexane, heptane, methanol, ethanol, isopropanol, dimethyl sulfoxide, acetone, ethyl acetate, diethyl ether, tert-butyl methyl ether, water, acetic acid, anisole, 1-butanol, 2-butanol, butane, butyl acetate, ethyl formate, formic acid, isobutyl acetate, isopropyl acetate, methyl acetate, 3-methyl-1-butanol, methylethyl ketone, 2-methyl-1-propanol, 1-pentanol, 1-propanol, propane, propyl acetate, trimethylamine, or a combination thereof.

26 . A method for converting tetrahydrocannabinolic acid (THCA) to cannabinolic acid (CBNA), the method comprising contacting the THCA with tetrachloro-1,4-benzoquinone at a temperature of between about 60° C. and about 130° C.

27 . The method of claim 14 , wherein the benzoquinone reagent comprises:

a compound as defined in formula (I) where X 1 ═H, X 2 ═H, X 3 ═H, and X 4 ═H,

a compound as defined in formula (I) where X 1 ═CN, X 2 ═CN, X 3 ═Cl, and X 4 ═Cl,

a compound as defined in formula (II) where X 1 ═H, X 2 ═C(CH 3 ) 3 , X 3 ═C(CH 3 ) 3 , and x 4 ═H,

a compound as defined in formula (II) where X 1 ═Cl, X 2 ═Cl, X 3 ═Cl, and X 4 ═Cl,

a compound as defined in formula (I) where X 1 ═Cl, X 2 ═Cl, X 3 ═Cl, and X 4 ═Cl,

a compound as defined in formula (II) where X 1 ═H, X 2 ═C(CH 3 ) 3 , X 3 ═H, and X 4 ═H,

a compound as defined in formula (I) where X 1 ═H, X 2═ OH, X 3 ═H, and X 4 ═H,

a compound as defined in formula (II) where X 1 ═H, X 2 ═C(CH 3 ) 3 , X 3 ═H, and X 4 ═OCH 3 , or

a compound as defined in formula (II) where X 1 ═H, X 2 ═H, X 3 ═H, and X 4 ═OCH 3 .

28 . The method of claim 24 , wherein the solvent is a protic solvent.

29 . The method of claim 24 , wherein the solvent is an aprotic solvent.