A method for producing 2,2′-bis(carboxymethoxy)-1,1′-binaphthyl includes performing steps (i) to (iv) below in sequence using a 2,2′-bis(alkoxycarbonylmethoxy)-1,1′-binaphthyl as a starting material: (i) a hydrolysis reaction step, (ii) a step of distilling off a resulting alcohol represented by formula (3) above from a reaction system, (iii) a step of acidifying a reaction solution, and (iv) a step of precipitating 2,2′-bis(carboxymethoxy)-1,1′-binaphthyl in the presence of an organic solvent.

A method for producing 2,2′-bis(carboxymethoxy)-1,1′-binaphthyl includes performing steps (i) to (iv) below in sequence using a 2,2′-bis(alkoxycarbonylmethoxy)-1,1′-binaphthyl as a starting material: (i) a hydrolysis reaction step, (ii) a step of distilling off a resulting alcohol represented by formula (3) above from a reaction system, (iii) a step of acidifying a reaction solution, and (iv) a step of precipitating 2,2′-bis(carboxymethoxy)-1,1′-binaphthyl in the presence of an organic solvent.

Provided are methods or processes for producing ferulic acid from a plant material, for example, a rice bran or its derivatives. Provided are methods comprising an ion swapping and solvent extraction process followed by a chromatographic separation operations that are coupled into a process which functions to recover a fraction rich in gamma-oryzanol, thus enabling the subsequent production of a high purity ferulic acid. Provided are methods comprising an ion swapping and solvent extraction process followed by a process which functions to recover a fraction rich in gamma-oryzanol, or a mixture of ferulic acid esters of phytosterols and triterpenoids, optionally comprising cycloartenyl ferulate, 24-methylenecycloartanyl ferulate, and/or campesteryl ferulate, to enable the production of a high purity ferulic acid. Provided are methods comprising a saponification and solvent extraction process followed by recovering a fraction rich in gamma-oryzanol to enable the production of a high purity ferulic acid.

Provided are methods or processes for producing ferulic acid from a plant material, for example, a rice bran or its derivatives. Provided are methods comprising an ion swapping and solvent extraction process followed by a chromatographic separation operations that are coupled into a process which functions to recover a fraction rich in gamma-oryzanol, thus enabling the subsequent production of a high purity ferulic acid. Provided are methods comprising an ion swapping and solvent extraction process followed by a process which functions to recover a fraction rich in gamma-oryzanol, or a mixture of ferulic acid esters of phytosterols and triterpenoids, optionally comprising cycloartenyl ferulate, 24-methylenecycloartanyl ferulate, and/or campesteryl ferulate, to enable the production of a high purity ferulic acid. Provided are methods comprising a saponification and solvent extraction process followed by recovering a fraction rich in gamma-oryzanol to enable the production of a high purity ferulic acid.

Methods of isolating phenols from phenol-containing media. The methods include combining a phospholipid-containing composition with the phenol-containing medium to generate a combined medium, incubating the combined medium to precipitate phenols in the combined medium and thereby form a phenol precipitate phase and a phenol-depleted phase, and separating the phenol precipitate phase and the phenol-depleted phase. The methods can further include extracting phenols from the separated phenol precipitate phase. The extracting can include mixing the separated phenol precipitate phase with an extraction solvent to solubilize in the extraction solvent at least a portion of the phenols originally present in the phenol precipitate phase.

Methods of isolating phenols from phenol-containing media. The methods include combining a phospholipid-containing composition with the phenol-containing medium to generate a combined medium, incubating the combined medium to precipitate phenols in the combined medium and thereby form a phenol precipitate phase and a phenol-depleted phase, and separating the phenol precipitate phase and the phenol-depleted phase. The methods can further include extracting phenols from the separated phenol precipitate phase. The extracting can include mixing the separated phenol precipitate phase with an extraction solvent to solubilize in the extraction solvent at least a portion of the phenols originally present in the phenol precipitate phase.

The present disclosure provides a process for the preparation of compounds of formula (III),

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compounds of formula (V),

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and corresponding salts of formula (IV).

##STR00003##

The compounds made by the methods and processes of the invention are particularly useful for administration in humans and animals.

The present disclosure provides a process for the preparation of compounds of formula (III),

##STR00001##

compounds of formula (V),

##STR00002##

and corresponding salts of formula (IV).

##STR00003##

The compounds made by the methods and processes of the invention are particularly useful for administration in humans and animals.

The present disclosure provides a process for the preparation of compounds of formula (III),

##STR00001##

compounds of formula (V),

##STR00002##

and corresponding salts of formula (IV).

##STR00003##

The compounds made by the methods and processes of the invention are particularly useful for administration in humans and animals.

Provided is a method for separating water-containing crystals, the method including: a step of generating water-containing crystals from a mixed liquid including water, acetic acid, and methacrylic acid; and a step of separating the crystals, in which the proportion by mass of methacrylic acid with respect to the total mass of water, acetic acid, and methacrylic acid in the mixed liquid is 0.09% by mass or more and less than 0.60% by mass.