Title:
METHOD FOR PRODUCING P-QUINONES
Document Type and Number:
WIPO Patent Application WO/2020/130080
Kind Code:
A1
Abstract:
The purpose of the present invention is to provide a method for synthesizing a p-quinone using one of alkoxy-substituted benzenes as a starting material. The present invention relates to a method for producing a compound of formula (II) (wherein R2, R3, R4 and R5 are as defined below) from a compound of formula (I) (wherein R1 represents an alkyl group; R2, R3, R4 and R5 may be the same or different, and each represents a hydrogen atom or an organic functional group; R2 and R3, and R4 and R5 may respectively combine with each other to form a ring, and the ring may have a substituent thereon; and R6 represents a hydrogen atom or the like) or the like. This method comprises a step for oxidizing a compound of formula (I) or the like in the presence of: a solvent that is selected from among water and a mixed solvent of water and an organic solvent; a persulfuric acid salt; and at least one compound that is selected from among 2-iodoxybenzoic acid, 2-iodosobenzoic acid, 2-iodobenzoic acid and the like.
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Inventors:
DOHI TOSHIFUMI (JP)
CHINA HIDEYASU (JP)
CHINA HIDEYASU (JP)
Application Number:
PCT/JP2019/049847
Publication Date:
June 25, 2020
Filing Date:
December 19, 2019
Export Citation:
Assignee:
RITSUMEIKAN TRUST (JP)
International Classes:
C07C46/02; C07B61/00; C07C50/02; C07C50/12
Other References:
TAKAYUKI YAKURA, TATSUYA KONISHI: "A novel catalytic hypervalent iodine oxidation of para-alkoxyphenols to para-quinones using 4-iodophenoxyacetic acid and Oxone", SYNLETT, no. 5, 8 March 2007 (2007-03-08), pages 765 - 768, XP055721158, ISSN: 0936-5214, DOI: 10.1055/s-2007-970758
TAKAYUKI YAKURA, YUAN TIAN, YÛ YAMAUCHI, MASANORI OMOTO, TATSUYA KONISHI: "Catalytic hypervalent iodine oxidation using 4-iodophenoxyacetic acid and Oxone: oxidation of p-alkoxyphenols to p-benzoquinones", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 57, no. 3, 5 January 2009 (2009-01-05), pages 252 - 256, XP055721165, ISSN: 0009-2363, DOI: 10.1248/cpb.57.252
ALEKSANDRA A. ZAGULYAEVA, CHRISTOPHER T. BANEK, MEKHMAN S. YUSUBOV, VIKTOR V. ZHDANKIN: "Hofmann Rearrangement of Carboxamides Mediated by Hypervalent Iodine Species Generated in Situ from Iodobenzene and Oxone: Reaction Scope and Limitations", ORGANIC LETTERS, vol. 12, no. 20, 15 September 2010 (2010-09-15), pages 4644 - 4647, XP055721169, ISSN: 1523-7060, DOI: 10.1021/ol101993q
S. L. COLLOM ,P. T. ANASTAS ,E. S. BEACH ,R. H. CRABTREE ,N. HAZARI ,T. J. SOMMER: "Differing selectivities in mechanochemical versus conventional solution oxidation using Oxone", TETRAHEDRON LETTERS, vol. 54, no. 19, 8 May 2013 (2013-05-08), pages 2344 - 2347, XP055721172, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2013.02.056
YAKURA T; OMOTO M; YAMAUCHI Y; TIAN Y; OZONO A: "Hypervalent iodine oxidation of phenol derivatives using a catalytic amount of 4-iodophenoxyacetic acid and Oxone as a co-oxidant", TETRAHEDRON, vol. 66, no. 31, 4 May 2010 (2010-05-04), pages 5833 - 5840, XP027122609, ISSN: 0040-4020, DOI: 10.1016/j.tet.2010.04.124
HIDEYASU CHINA , KOKORO TANIHARA , HIROTAKA SASA , KOTARO KIKUSHIMA, TOSHIFUMI DOHI: "Regiodivergent oxidation of alkoxyarenes by hypervalent iodine/oxone system", CATALYSIS TODAY, vol. 348, 15 May 2019 (2019-05-15), pages 1 - 7, XP055721175, ISSN: 0920-5861, DOI: 10.1016/j.cattod.2019.08.060
TAKAYUKI YAKURA, YUAN TIAN, YÛ YAMAUCHI, MASANORI OMOTO, TATSUYA KONISHI: "Catalytic hypervalent iodine oxidation using 4-iodophenoxyacetic acid and Oxone: oxidation of p-alkoxyphenols to p-benzoquinones", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 57, no. 3, 5 January 2009 (2009-01-05), pages 252 - 256, XP055721165, ISSN: 0009-2363, DOI: 10.1248/cpb.57.252
ALEKSANDRA A. ZAGULYAEVA, CHRISTOPHER T. BANEK, MEKHMAN S. YUSUBOV, VIKTOR V. ZHDANKIN: "Hofmann Rearrangement of Carboxamides Mediated by Hypervalent Iodine Species Generated in Situ from Iodobenzene and Oxone: Reaction Scope and Limitations", ORGANIC LETTERS, vol. 12, no. 20, 15 September 2010 (2010-09-15), pages 4644 - 4647, XP055721169, ISSN: 1523-7060, DOI: 10.1021/ol101993q
S. L. COLLOM ,P. T. ANASTAS ,E. S. BEACH ,R. H. CRABTREE ,N. HAZARI ,T. J. SOMMER: "Differing selectivities in mechanochemical versus conventional solution oxidation using Oxone", TETRAHEDRON LETTERS, vol. 54, no. 19, 8 May 2013 (2013-05-08), pages 2344 - 2347, XP055721172, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2013.02.056
YAKURA T; OMOTO M; YAMAUCHI Y; TIAN Y; OZONO A: "Hypervalent iodine oxidation of phenol derivatives using a catalytic amount of 4-iodophenoxyacetic acid and Oxone as a co-oxidant", TETRAHEDRON, vol. 66, no. 31, 4 May 2010 (2010-05-04), pages 5833 - 5840, XP027122609, ISSN: 0040-4020, DOI: 10.1016/j.tet.2010.04.124
HIDEYASU CHINA , KOKORO TANIHARA , HIROTAKA SASA , KOTARO KIKUSHIMA, TOSHIFUMI DOHI: "Regiodivergent oxidation of alkoxyarenes by hypervalent iodine/oxone system", CATALYSIS TODAY, vol. 348, 15 May 2019 (2019-05-15), pages 1 - 7, XP055721175, ISSN: 0920-5861, DOI: 10.1016/j.cattod.2019.08.060
Attorney, Agent or Firm:
SAEGUSA & PARTNERS (JP)
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