Method of preparing 4-(.alpha.-alkyl-.alpha.-cyano-methyl)2,6-di

Details Method of preparing 4-(.alpha.-alkyl-.alpha.-cyano-methyl)2,6-di Method of preparing 4-(.alpha.-alkyl-.alpha.-cyano-methyl)2,6-di

1982-06-07

1983-09-20

Torrence, Dolph H.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

562478, C07C12175, C07C 5911

Patent

active

044055285

ABSTRACT:
4-(.alpha.-alkyl-.alpha.-cyano-methyl)2,6-di-substituted phenols having the formula ##STR1## wherein R is methyl, ethyl, n-propyl or isopropyl are prepared by reacting a di-substituted phenol, such as 2,6-di-tertiary-butyl phenol, with a Friedel-Crafts addition agent in the presence of a Friedel-Crafts catalyst such as aluminum chloride to form the corresponding 4-(.alpha.-alkyl-.alpha.-oxo-methyl)2,6-di-substituted phenol. The 4-(.alpha.-alkyl -.alpha.-oxo-methyl)2,6-di-substituted phenol thus formed readily can be reduced to form the corresponding 4-(.alpha.-alkyl-.alpha.-hydroxy-methyl)2,6-di-substituted phenol which thereafter can be reacted with an alkali metal or an alkaline earth metal cyanide to form the desired 4-(.alpha.-alkyl-.alpha.-cyano-methyl)2,6-di-substituted phenol. This can be converted by hydrolysis into the corresponding .alpha.-alkyl-4-hydroxyphenylacetic acid. These acids are well-known insecticidal and acaricidal intermediates.

REFERENCES:
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Volod'kin et al., Iz. Akad. Nauk. SSSR, Ser. Khim, 1030-1032, (1966).
Kudinova et al., Iz. Akad. Nauk. SSSR, Ser. Khim, 1313-1317, (1978).
Schwartz et al., J. Org. Chem., vol. 41, 2502 (1976).
Hay, J. Org. Chem., vol. 34, 1160 (1969).
Advanced Organic Chemistry, (McGraw-Hill, New York, 1977), pp. 809-810.

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