Preparation of cyanophenols

Details Preparation of cyanophenols Preparation of cyanophenols

1974-02-15

1976-01-20

Winters, Sherman D.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2602396, 2602397, 2602398, 2602471R, 2602477A, 2602477K, 260279R, 260283R, 260289R, 26029373, 26029375, 26029377, 2602948F, 2602949, 2603265SF, 2603265J, 260329R, 2603323R, 260335, 2603472, 2603478, 2603976, 260456P, 260465R, 260465D, 260465E, 260465F, 260471R, 260521R, 260591, 260592, 260607A, 424248, 424258, 424263, 424267, 424274, 424275, 424285, 424303, 424304, 424308, 424317, C07D27934

Patent

active

039338070

ABSTRACT:
A process for the preparation of a cyanophenol of formula (I) ##SPC1##
wherein Z is a substituent in the 4- or 6-position with respect to the hydroxy group, characterized in that cyanide ions are reacted in a dipolar aprotic solvent with a nitrobenzene of formula (II) ##SPC2##
wherein Z has the same value as in formula (I) and is a group, other than a nitro group, known to withdraw electrons in substitution reactions and which does not contain a proton capable of ionizing under the defined reaction conditions if such ionization would inhibit the electron-withdrawing effect of the group Z.
In formula (I) and (II) the benzene ring is optionally substituted by one or more non electron-withdrawing groups, or by one or more electron-withdrawing groups provided that such electron-withdrawing groups are in positions other than the 4- and 6-positions with respect to the hydroxy group.
The compounds of formula (I) are of value in being readily hydrolysed to the corresponding salicylic acids of formula (III) ##SPC3##
certain of which have been described in the literature as possessing a variety of pharmacological properties.

REFERENCES:
chemical Communications (1971) pp. 1120-1121 Gorvin.

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