Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1997-12-03
1998-09-15
Geist, Gary
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568338, C07C 4543
Patent
active
058081666
DESCRIPTION:
BRIEF SUMMARY
This is the U.S. National Stage Application of PCT/JP97/01133 filed Apr. 2, 1997 now WO 97/37961 published Oct. 16, 1997.
TECHNICAL FIELD
The present invention relates to a method for producing 3,4-dihydroxy-3-cyclobutene-1,2-dione.
3,4-Dihydroxy-3-cyclobutene-1,2-dione (usual name: squaric acid) is useful as a raw material for functional materials of medicines, electrophotographic photoreceptors, recording materials for rewritable optical discs, photosensitizers, etc. (Chem. Rev., 93, 449 (1993); Japanese Published Unexamined Patent Application Nos. 5-306285, 2-306247, 2-48665, 5-5005, and 5-96173).
BACKGROUND ART
Various methods for producing 3,4-dihydroxy-3-cyclobutene-1,2-dione have heretofore been known. However, the known methods are problematic in that the process for those is complicated and takes much time, that the starting materials for those are difficult to synthesize, that they require strict conditions, that their yield is low, and that they require special equipment. For example, the known methods include (1) a method of using triketene as the starting material (B. Jackson et al., EP 442431); (2) a method of using 3-hydroxy-3-cyclobutene-1,2-dione as the starting material (D. Bellus et al., Helv. Chim. Acta, 61, 1784 (1978)); (3) a method of using tetraalkoxyethylene as the starting material (D. Bellus, J. Org. Chem., 44, 1208 (1979)); (4) a method of using dialkoxyacetylene as the starting material (M. A. Pericas, Tetrahedron Letter, 4437 (1977)); (5) a method of using tetrahalogenoethylene as the starting material (J. Amer. Chem. Soc., 81, 3480 (1959)); (6) a method of using hexachlorobutadiene as the starting material (P. Hagenberg et al., Ger. Offen. 1568291); and (7)a method of using carbon monoxide as the starting material (G. Silvestri et al., Electrochim. Acta, 23, 413 (1978)). However, those methods are all problematic in that, in (1), it is difficult to ensure a large quantity of the starting material, triketene, which is a side product in the production of diketene; in (2), the starting material is obtained in biological solid cultivation with poor productivity or in chemical synthesis that requires a complicated and long process; in (3), the starting material is difficult to produce, and its yield is low; in (4), the starting material is difficult to produce; in (5), the starting material is difficult to produce, and its production requires a complicated and long process; in (6), the yield of the product is low; and in (7), the production requires special equipment.
DISCLOSURE OF THE INVENTION
The present invention relates to a method for producing 3,4-dihydroxy-3-cyclobutene-1,2-dione of general formula (II): ##STR2## which comprises hydrolyzing a 3-alkoxy-2,2,4,4-tetrahalogenocyclobutanone derivative of general formula (I): ##STR3## wherein R.sup.1 represents alkyl, and R.sup.2, R.sup.3 and X independently represent halogen.
The present invention also relates to a method for producing 3-alkoxy-2,2,4,4-tetrahalogenocyclobutanone derivatives of formula (I): ##STR4## wherein R.sup.1, R.sup.2, R.sup.3 and X have the same meanings as above, which comprises halogenating a 3-alkoxy-2,2-dihalogenocyclobutanone derivative of general formula (III): ##STR5## wherein R.sup.1, R.sup.2 and R.sup.3 have the same meanings as above, with a halogenating agent.
The present invention further provides 3-alkoxy-2,2,4,4-tetrahalogenocyclobutanone derivatives of formula (I): ##STR6## wherein R.sup.1, R.sup.2, R.sup.3 and X have the same meanings as above.
Compounds of formulae (I), (II) and (III) are hereinafter referred to as compound (I), compound (II) and compound (III), respectively.
In the definitions of the groups in formulae (I) and (II), the alkyl means a straight-chain or branched alkyl group having 1 to 18 carbon atoms, including methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isoamyl, neopentyl, 2-pentyl, 3-pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl, dodecyl, pentadecyl and octadecyl; and the halogen means fluorine, chlorine, bromine
REFERENCES:
patent: 4997745 (1991-03-01), Kawamura et al.
patent: 5391741 (1995-02-01), Shimizu et al.
Bellus et al, Helvetica Chimica Acta, vol. 61, No. 173 (1978) 1784-1813.
Bellus et al, J. Org. Chem., vol. 44, No. 8 (1979) 1208-1211.
Pericas et al, Tetrahedron Letters, No. 50 (1977) 4437-38.
Silvestri et al, Electrochimica Acta., vol. 23 (1978) 413-417.
Law et al, Chem. Rev., vol. 93 (1993) 449-486.
Matsushita Shoshiro
Okajima Asako
Shimizu Ikuo
Toyoda Hiroshi
Usami Takeshi
Geist Gary
Kyowa Yuka Co., Ltd.
Padmanabhan Sreeni
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