Process for the preparation of 3-Hydroxyisoxazole Compounds and Alkali Metal Salts thereof

1,199,737. 3-Hydroxyisoxazoles. SANKYO CO. Ltd. 18 Aug., 1967, No. 38087/67. Heading C2C. 3-Hydroxyisoxazoles of the formula wherein R represents hydrogen or an alkyl, phenyl, substituted phenyl, carboxyl or dialkoxymethyl group having 1-5 carbon atoms in each alkoxy moiety, and the alkali metal salts thereof, are prepared by reacting hydroxylamine, or an acid addition salt thereof, with either a compound of the formula where R11 is hydrogen, or an alkyl, phenyl, substituted phenyl, alkoxycarboxyl, the alkoxy moiety containing 1-3 carbon atoms, or dialkoxy methyl group, R1 is a C 1-5 alkyl group, and X is halogen, or a compound of the formula where Y and Z are different and represent hydrogen or halogen, in the presence of an alkali metal hydroxide to form the alkali metal salt of the hydroxyisoxazole and, if desired, treating the salt with an organic or inorganic acid to liberate the free hydroxy compound, the alkali metal hydroxide being used in an amount of at least 3 mols. per mol. of dihalo reactant or at least 2 mols. per mol. of olefinic reactant. The reaction is preferably effected at 30-120‹ C. in an inert solvent using 1-1À5 mol. hydroxylamine per mol. dihalo or olefinic reactant. Examples relate to the preparation of 5-methyl, 5-isopropyl, 5-phenyl, 5-(4-rnethylphenyl), 5-(4- chlorophenyl), 5-(41-biphenylyl), 5-(4-methoxyphenyl), 5-(4-nitrophenyl), 5-diethoxymethyl, 5-ethyl, 5-isobutyl, 5-n-decyl, 5-n-propyl, 5- carboxy-, 5-(4-cyanophenyl), 5-(3-nitrophenyl) and 5-(2-methoxyphenyl)-3-hydroxyisoxazoles.