Single-vessel process for preparing 2-acetaminonaphthalene-6-sul

Details Single-vessel process for preparing 2-acetaminonaphthalene-6-sul Single-vessel process for preparing 2-acetaminonaphthalene-6-sul

1988-11-10

1990-03-13

Chan, Nicky

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

Organic compounds

Sulfonic acids or salts thereof

C07C14360

Patent

active

049084780

ABSTRACT:
A single-vessel process for preparing 2-acetaminonaphthalene-6-sulfonic acid of high purity by sulfonating 2-hydroxynaphthalene with concentrated sulfuric acid, converting the 2-hydroxynaphthalenesulfonic acid formed with ammonia in the presence of ammonium hydrogensulfite into 2-amino-naphthalene-6-sulfonic acid (Bucherer reaction) and N-acetylating the latter to give 2-acetaminonaphthalene-6-sulfonic acid, which comprises, after diluting the sulfonating melt with water, substantially removing any impurities still present in the resulting aqueous solution of 2-hydroxynaphthalene-6-sulfonic acid, in particular 2-hydroxynaphthalene, by extraction with toluene or xylene and/or clarification using active carbon.

REFERENCES:
Drake, "The Bucherer Reaction" in Organic Reactions, vol. 1, John Wiley & Sons, Inc., N.Y., N.Y., 1942, p. 105 ff.
Shine, Aromatic Rearrangements, Elsevier Pub., N.Y. (The Bucherer Reaction), 1967, p. 207 ff.
Angewandte Chemie, 79, 329-388 (1967).

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