Process for the manufacture of 6-chloro-1,4-diacetoxy-2,3-dimeth

Details Process for the manufacture of 6-chloro-1,4-diacetoxy-2,3-dimeth Process for the manufacture of 6-chloro-1,4-diacetoxy-2,3-dimeth

1985-10-24

1990-06-12

Garner, Vivian

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

Organic compounds

Carboxylic acid esters

552297, 552307, 568633, C07C 6708, C07C 6916

Patent

active

049334891

ABSTRACT:
An improved process for the manufacture of the antipsoriatic agent, 6-chloro-1,4-diacetoxy-2,3-dimethoxynaphthalene, is herein described which involves in situ Diels-Alder coupling of 2,3-dimethoxybenzo-1,4-quinone with a 3-chloro-1-alkoxy-1,3-butadiene; 1,4-elimination of the alcohol with aromatization of the chlorine-bearing ring, and acetylation.

REFERENCES:
patent: 4482492 (1984-11-01), Kiefer
patent: 4533554 (1985-08-01), Terao et al.
Weygand et al., Synthesis of O-Diacylbenzenes, Phthalides and Naphthoguinones, Chem. Ber., 90(9), 1884-87, 1985(1957). (Excerpts translated).
Fieser et al., J. Amer. Chem. Soc., 71, 3615 (1949).
Synthesis of o-Diacylbenzenes, Phthalides and Napthoquinones Chemische Berichte, 90 Jahrg./1957/Nr.9 pp. 1879-1895.
Chem. Abstracts, 9-30-74, vol. 81, No. 13, 77377, p. 418 paragraph 6 E.P.O. Search Report, Appln. No. 86 114 796.5.

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