Preparation of catechol derivatives

Details Preparation of catechol derivatives Preparation of catechol derivatives

1976-12-01

1978-04-25

Gotts, Lewis

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260609D, 260327M, 560130, 260516, 2603405R, C07C15309, C07C14930, C07C 6708

Patent

active

040862658

ABSTRACT:
A method of preparing derivatives of aromatic compounds including the catechol function ##STR1## by replacement of one of the hydroxyls by mercaptan ##STR2## Cathechol or a multi-ring compound (naphthyl-, anthryl-, phenanthryl-, etc.) containing the catechol function is first reacted with thiophosgene to produce the corresponding dioxole-2-thione ##STR3## The thione is ammonolyzed to the corresponding hydroxy N,N-disubstituted thionocarbamate ##STR4## The thionocarbamate is acetylated to ##STR5## and heated to rearrange the compound to the corresponding thiolcarbamate ##STR6## Further heating produces the corresponding oxathiol-2-one ##STR7## which can be hydrolyzed to the corresponding mercaptan ##STR8##

REFERENCES:
patent: 1968905 (1934-08-01), Palmer
patent: 1968906 (1934-08-01), Palmer
patent: 2004728 (1935-06-01), Palmer
H. R. Al-Kazimi et al., J. Amer. Chem. Soc., 77,2479, (1955).
H. Kwart et al., J. Org. Chem., 31, 410, (1966).
M. S. Newman et al., J. Org. Chem., 31, 3980, (1966).

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