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US 2024/0132430 A1Published application
Chemicals and use of hypohalites in mechanism-based selective dual radical organic synthesis
AssigneeWalker Cancer Research Institute, Inc.
InventorEduardo PALOMINO
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Abstract
The synthesis of pattern-specific compounds using hypohalites, such as hypochlorous acid, sodium hypochlorite, and potassium hypoiodite, as dual-radical generators is provided. The synthesis can be implemented by a cyclization reaction, a dehydrogenation reaction, a hydroxylation reaction, a decarboxylation reaction, or any combination of the above four. The reactions are typically carried out in water, in a nonpolar solvent such as ethyl acetate, or a mixture of both. Hypochlorous acid is made by adding a weak acid such as acetic acid to sodium hypochlorite.
Claims30
A method comprising:
- forming a biphasic mixture including an aqueous phase that includes a hypochlorite salt and an organic phase that includes a nonpolar solvent and a 5,7,8-trimethyl-6-chromanol described by formula 1;
- agitating the biphasic mixture to allow a reaction between the hypochlorite salt and a 5,7,8-trimethyl-6-chromanol described by formula 1;
- collecting the organic phase;
- and
- removing the nonpolar solvent to recover a p-quinones described by formula 2:
- wherein R is selected from linear or branched C1-22 alkyl, HC═O, or carboxy.
3 more elements
A method comprising:
- combining an aqueous solution that includes a hypochlorite salt with a nonpolar solvent to form a biphasic mixture including an organic phase and an aqueous phase;
- adding a weak organic acid to the biphasic mixture to form hypochlorous acid;
- agitating the biphasic mixture such that the hypochlorous acid is transferred from the aqueous phase to the organic phase;
- discarding the aqueous phase;
- adding a catecholamine described by formula 3 to the organic phase that includes the hypochlorous acid;
- and
- removing the nonpolar solvent to recover an aminochrome described by formula 4:
- wherein:
- R1, R2 are each independently H, alkyl, or alkoxy.
6 more elements
A method for making catechols comprising:
- forming a biphasic mixture including an aqueous phase that includes a hypochlorite salt and an organic phase that includes a nonpolar solvent;
- adding a weak organic acid to the biphasic mixture to form hypochlorous acid in the aqueous phase;
- agitating the biphasic mixture to transfer the hypochlorous acid formed in the aqueous phase into the organic phase;
- discarding the aqueous phase;
- adding a chromanol described by formula 5 to the organic phase;
- agitating the organic phase until an acidic aqueous phase is formed, the acidic aqueous phase including hydrochloric acid (HCl);
- discarding the acidic aqueous phase;
- removing the nonpolar solvent;
- and
- collecting a catechol described by formula 6:
- wherein R is selected from linear or branched C1-22 alkyl, HC═O, or carboxy. solvent.
8 more elements
A method comprising:
- forming a biphasic mixture including an aqueous phase that includes a hypochlorite salt and an organic phase that includes a nonpolar solvent;
- adding a weak organic acid to the biphasic mixture to form hypochlorous acid;
- agitating biphasic mixture such that the hypochlorous acid is transferred from the aqueous phase to the organic phase;
- discarding the aqueous phase;
- adding a p-aminophenol described by formula 7 to the organic phase to form a p-imino quinone described by formula 8;
- and
- removing the nonpolar solvent and any water therein to recover the p-imino quinone described by formula 8 thereof:
- wherein R1, R2, R3 and R4 are each independently H, alkyl, or alkoxy. solvent.
5 more elements
A method comprising:
- reacting a ketone described by formula 9 with a hypochlorite salt to form a trichloromethyl ketone described by formula 10;
- and
- collecting the trichloromethyl ketone described by formula 10, wherein
- if the ketone described by formula 9 is water soluble, the ketone described by formula 9 is mixed into an aqueous hypochlorite salt solution;
- and
- if the ketone described by formula 9 is water insoluble, the ketone described by formula 9 is mixed into a nonpolar solvent and combined with an aqueous hypochlorite salt solution to form a biphasic mixture, the biphasic mixture is then agitated to provide a reaction for form the trichloromethyl ketone described by formula 10:
- wherein R is linear or branched C1-22 alkyl.
4 more elements
A method comprising:
- combining an aqueous solution that includes a hypochlorite salt with a nonpolar solvent to form a biphasic mixture including an organic phase and an aqueous phase;
- adding a weak organic acid to the biphasic mixture to form hypochlorous acid;
- agitating the biphasic mixture to transfer the hypochlorous acid from the aqueous phase to the organic phase;
- adding an ascorbic acid described by formula 11 to the organic phase;
- agitating the mixture until all of the solid ascorbic acid has reacted and is incorporated into the organic phase;
- discarding a bottom layer that includes hydrochloric acid;
- and
- removing the nonpolar solvent to recover a compound described by formula 12:
5 more elements
Dependencies are inferred from the claim text.