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Title:
PRODUCTION OF 1,4-DIACETOXY-2-METHYLNAPHTHALENE
Document Type and Number:
Japanese Patent JPH0710804
Kind Code:
A
Abstract:

PURPOSE: To produce the subject compound in high hyield industrially by subjecting 2-methyl-1,4-naphthoquinone and 6-methyl-1,4-naphthoquinone and a conjugated diene to Diels-Alder reaction, acetylating the resulting substance under a reducing condition, then isolating.

CONSTITUTION: A mixture of 2-methyl-1,4-naphthoquinone of formula I obtained by oxidizing 2-methylnaphthalene and 6-methyl-1,4-naphthoquinone of formula II is subjected to Diels-Alder reaction with a conjugated diene (e.g. cyclopentadiene) to give a mixture of the compound of formula I and 6- methyl-1,4,4a,9a-tetrahydro-1,4-methanoanthraquinone of formula IV. Then, this mixture is acetylated under a reducing condition and then isolated to give the objective 1,4-diacetoxy-2-methylnaphthalene of formula III. The compound of formula III is vitamin K1 useful as a hemostatic vitamin and is suitable as an intermediate for manatetrenone (vitamin K2) useful as a therapeutic agent for hypoprothrombinemia of newborn infant, intrapartum hemorrhage and hypoprothrombinemia occurring during administration of antibiotic.


Inventors:
HAYASHI TSUGUNORI
TSUJII MASAHIKO
Application Number:
JP17356793A
Publication Date:
January 13, 1995
Filing Date:
June 22, 1993
Export Citation:
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Assignee:
EISAI KAGAKU KK
International Classes:
C07B61/00; C07C46/04; C07C50/10; C07C67/29; C07C69/16; (IPC1-7): C07C69/16; C07C67/29