Synthesis of 4,6-diaminoresorcinol

Details Synthesis of 4,6-diaminoresorcinol Synthesis of 4,6-diaminoresorcinol

1993-10-15

1994-12-06

Raymond, Richard L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

562 78, 562 81, 564443, 568709, 568765, C07C20936

Patent

active

053712919

ABSTRACT:
The invention is a new process for preparing 4,6-diaminoresorcinol, a precursor to polybisbenzoxazoles. The desired product is prepared from resorcinol by incorporating a halo group on the 2-position of resorcinol to form 2-haloresorcinol, then nitrating selectively at the 4- and 6-positions of the 2-haloresorcinol to form 2-halo-4,6-dinitroresorcinol, then hydrogenating the 2-halo-4,6-dinitroresorcinol. The selective incorporation of a halo group on the 2-position of resorcinol is accomplished by sulfonating resorcinol at the 4- and 6-positions. The following scheme illustrates the synthetic route used to prepare 4,6-diaminoresorcinol from resorcinol: ##STR1##

REFERENCES:
patent: 3903178 (1975-09-01), Nakamura et al.
patent: 4038328 (1977-07-01), Pelster et al.
patent: 4704469 (1987-11-01), Valle
patent: 4766244 (1988-08-01), Lysenko
patent: 4982001 (1991-01-01), Lysenko et al.
"Polybenzothiazoles and Polybenzoxazoles" listed in The Encyclopedia of Polymer Science and Engineering vol. 11 pp. 601-635, .COPYRGT. 1988 by John Wiley & Sons, Inc.
"Anthracene Derivatives" by M. V. Gorelik listed in J. Gen. Chem. USSR 1964, 34, p. 2028.

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