Synthesis of perhalomethylcarbinol-substituted phenol and naphth

Details Synthesis of perhalomethylcarbinol-substituted phenol and naphth Synthesis of perhalomethylcarbinol-substituted phenol and naphth

1978-11-02

1981-03-10

Rizzo, Nicholas S.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

544 62, 546198, 548207, 548210, 544133, 544135, C07D27504

Patent

active

042555787

ABSTRACT:
The present invention is concerned with a method of synthesizing certain ##STR1## 3-disubstituted sulfam(na)phthalein compounds useful as pH-sensitive indicator dyes and with intermediates useful in the preparation of said compounds. The subject method comprises (1) reacting (a) a 3,3-disubstituted sulfam(na)phthalein wherein one of the 3-substituents is a 4'-hydroxy-1'-phenyl moiety or a 4'-hydroxy-1'-naphthyl moiety substituted in the 3'-position with a perhalomethylcarbinol group and (b) an acid halide, ##STR2## wherein R is alkyl or aryl to give (c) an acylated intermediate wherein the N atom of the sulfam(na)phthalein ring and the 4'-hydroxy and carbinol hydroxy groups are acylated with ##STR3## and (2) treating said compound (c) with alkali to selectively remove said ##STR4## from said hydroxy groups and yield the ##STR5## product. The intermediates of the present invention are the acylated compounds (c).

REFERENCES:
Abramovitch, R., J. Chem. Soc., Perkin Trans. I, 1974 (22) p. 2589.
Mustafa, A., J. Chem. Soc., (1952), p. 1339.
Dutt, J. Chem. Soc., 121, p. 2389 (1922).
Beilstein "Handbuch der Organischen Chemie", vol. 27, p. 534.
Bartlett, R. et al., J. Chem. Soc., 1939, 760-762.
Morrison, R. et al., "Organic Chemistry", 3rd ed., Allyn & Bacon, Inc., Boston, 1974, pp. 677 & 794.
Ber. 29 p. 1049 (1896).

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