Resolution of 2-(6-methoxy-2-napthyl)propionic acid

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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260DIG8, 260284, C07B 2100, C07B 1900, C07C 5142

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active

039883655

ABSTRACT:
Resolution of mixtures of d and 1,2-(6-methoxy-2-napthyl)propionic acid with cinchonidine to yield the d-isomer is conducted by using, in combination with the cinchonidine, an inorganic base having a basicity, pKa, greater than 8 and forming a salt of 2-(6-methoxy-2-napthyl)propionic acid more soluble than the solubility of the corresponding cinchonidine salts. After the cinchonidine salt product is cleaved by treatment with a strong base at about room temperature in methanol, the methanolic solution is mixed with sufficient water to precipitate the cinchonidine in a form which is easy to filter. After removal of the precipitated cinchonidine, acidification yields a product enriched in d 2-(6-methoxy-2-napthyl)propionic acid.

REFERENCES:
patent: 3683015 (1972-08-01), Dyson
patent: 3904683 (1975-09-01), Day et al.
Gilman, "Org. Chem.," Wiley & Sons, Inc., N.Y. (1958) pp. 256-258.

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