Method of preparing 4-(.alpha.-hydrocarbyl-.alpha.-cyanomethyl)2

Details Method of preparing 4-(.alpha.-hydrocarbyl-.alpha.-cyanomethyl)2 Method of preparing 4-(.alpha.-hydrocarbyl-.alpha.-cyanomethyl)2

1983-07-20

1984-12-11

Torrence, Dolph H.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260465D, 260465E, 562478, C07C12175, C07C 6966

Patent

active

044877226

ABSTRACT:
4-(.alpha.-hydrocarbyl-.alpha.-cyanomethyl)2,6-di-hydrocarbyl-substituted phenols having the formula ##STR1## wherein R.sub.1 and R.sub.2 are the same or different monovalent substituents selected from the group consisting of alkyl, aralkyl and cyclic alkyl radicals and R.sub.3 is selected from hydrogen, hydrocarbyl radicals, substituted hydrocarbyl radicals and hydrocarbyloxy radicals are prepared by reacting an N,N-di-hydrocarbyl-4-(.alpha.-hydrocarbyl-.alpha.-aminomethyl)2,6-di-hydro carbyl-substituted phenol having the formula ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined above and R.sub.4 and R.sub.5 are the same or different and are selected from hydrogen, hydrocarbyl radicals and substituted hydrocarbyl radicals with an alkali metal cyanide or an alkaline earth metal cyanide in a suitable solvent. The 4-(.alpha.-hydrocarbyl-.alpha.-cyanomethyl)2,6-di-substituted phenol thus formed can readily be converted to the corresponding 4-(.alpha.-hydrocarbyl-.alpha.-cyanomethyl)phenol by dealkylating the substituent groups ortho to the hydroxyl group from the 4-(.alpha.-hydrocarbyl-.alpha.-cyanomethyl)2,6-di-substituted phenol which then can be converted on hydrolysis to the corresponding .alpha.-hydrocarbyl-4-hydroxyphenylacetic acid. These acids have utility as insecticidal and acaricidal intermediates and are deemed to have utility as insecticides themselves as are the 4-(.alpha.-hydrocarbyl-.alpha.-cyanomethyl)2,6-di-substituted phenols of the present invention.

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