Preparation process for hydroxyphenylacetic acids

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof

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562465, C07C 6501

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053959647

ABSTRACT:
Preparation process for a hydroxyphenylacetic acid of formula (I): ##STR1## where R.dbd.H, alkyl or alkoxyl as well as its salts, in which the corresponding free or salified hydroxymandelic acid of formula (II): ##STR2## in which R has the meaning given previously and M.dbd.H, K or an ammonium group is reacted in an aqueous medium, at a temperature greater than or equal to 50.degree. C., with formic acid in the presence of catalytic quantities of an oxygenated derivative of sulphur having a degree of oxidation from 2 to 4, in order to obtain the hydroxyphenylacetic acid of formula (I) which is isolated or, if desired, is salified according to the usual methods and the hydroxyphenylacetic acid thus obtained.

REFERENCES:
patent: 5145994 (1992-09-01), Mandal et al.
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Robinson et al., Hydroxycarboxlyic Acids, C.sub.8 H.sub.8 O.sub.3 -3-Hydroxyphenylacetic acid, C.sub.8 H.sub.8 O.sub.3, J. Chem. Soc., vol. 1927, p. 2412.
Baeyer et al., Hydroxycarboxylic Acids, C.sub.8 H.sub.8 O.sub.3 -2-Hydroxyphenylacetic acid, 2-hydroxy-.alpha.-toluic acid, C.sub.8 H.sub.8 O.sub.3, Ber., vol. 17, p. 974; Fritsch, doctoral dissertation (Munich, 1888), p. 16.
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McKenzie et al., Hydroxy-(2-hydroxyphenyl)acetic acid, 2-hydroxymandelic acid; C.sub.8 H.sub.8 O.sub.4, J. Chem. Soc., vol. 1935, pp. 104 & 111.
Hahn et al., 3-Hydroxy-DL-mandelic acid nitrile, 3-hydroxy-DL-mandelonitrile, C.sub.8 H.sub.7 NO.sub.2, BER., vol. 71, pp. 2154, 2158, & 2162, (1938), Cf. E 11, 270.
Pratesi et al., Hydroxyphenyl-(4-hydroxyphenyl)acetic acid, 4-hydroxymandelic acid, C.sub.8 H.sub.8 O.sub.4, Farmaco, Ed. Scient., vol. 10, pp. 563 & 569, 1955.
Shaw et al., 3-Hydroxy-DL-mandelic acid, C.sub.8 H.sub.8 O.sub.4, formula II (R=R'=X=H), J. Org. Chem. vol. 21, p. 1149, 1956.
Shaw et al., 3-Hydroxy-DL-mandelonitrile, C.sub.8 H.sub.7 NO.sub.2, J. Org. Chem., vol. 21, p. 1149, 1956.

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