Process for producing cyclopropylphenol derivative

Details Process for producing cyclopropylphenol derivative Process for producing cyclopropylphenol derivative

2006-03-31

2009-12-08

Witherspoon, Sikarl A (Department: 1621)

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

Organic compounds

Oxygen containing

C560S103000

Reexamination Certificate

active

07629494

ABSTRACT:
A process for producing a cyclopropylphenol represented by of formula (10):wherein R1, R2, R3and R4each may represent a hydrogen; Z represents a hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or phenyl; and Y1, Y2and Y3each may represent a hydrogen; by reacting a compound of formula (7):wherein X represents a halogen; and V represents a hydrogen or —W—R5,with a metal, metal salt or organometallic compound of formula (8): M2to obtain a compound of formula (9):and obtaining a compound of formula (10) by hydrolysis in the case wherein V represents —W—R5, wherein W is CO, SO or SO2and R5is alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, phenyl, alkoxy or haloalkoxy.

REFERENCES:
patent: 2005/0037925 (2005-02-01), Tsukamoto et al.
patent: 2-256684 (1990-10-01), None
patent: 2004-002263 (2004-01-01), None
patent: WO 03/016286 (2003-02-01), None
Thomas F. Corbin et al., “Cyclopropylbenzene,”Organic Syntheses, 1964, vol. 44, pp. 30 to 33.
Roger C. Hahn et al., “Electrical Effects of Cycloalkyl Groups1,”Journal of the American Chemical Society, 1968, vol. 90, No. 13, pp. 3404 to 3415.
T.W. Greene et al., “Protection for Phenols and Catechols,”Protective Groups in Organic Synthesis, Third Edition, 1999, pp. 276 to 287.
J.J. Talley et al., “Reaction of Lithiumo-Lithiophenoxide with Carbonyl Compounds,”The Journal of Organic Chemistry, 1984, vol. 49, No. 26, pp. 5267 to 5269.
Torsten Herbertz et al., “Oxidation of Aryl- and Diarylcyclopropanes in a Pentasil Zeolite: Ring Opening with Deprotonation or Net Hydrogen Migration,”Eur. J. Org. Chem., 2000, pp. 467 to 472.
S. Walia et al., “Cyclopropyl MDP Compounds as New Pyrethrum Synergists,”Agric. Biol. Chem., 1984, 48(11), pp. 2675 to 2679.
Tohru Kitamura et al., “Photochemical Reactions of Allylphenoxide Anions,”Tetrahedron, 1978, vol. 34, pp. 3451 to 3457.
John A. Soderquist et al., “Aryl and Vinyl Cyclopropanes Through the In Situ Generation ofB-cyclopropy1-9-BBN and its Suzuki-Miyaura Coupling,”Tetrahedron Letters, 41, (2000), pp. 4251 to 4255.
José Barluenga et al., “Diastereo- and Enantioselective Carbolithiation of Allylo-Lithioaryl Ethers. New Chiral cyclopropane Derivatives,”Organic Letters, (2002), vol. 4, No. 13, pp. 2225 to 2228.
Debra J. Wallace et al., “Cyclopropylboronic Acid: Synthesis and Suzuki Cross-Coupling Reactions,”Tetrahedron Letters, 43, (2002), pp. 6987 to 6990.
Fachuang Lu et al., “The DFRC Method for Lignin Analysis. 7. Behavior of Cinnamyl End Groups,”J. Argic. Food Chem., (1999), vol. 47, No. 5, pp. 1981 to 1987.
Joseph Paul Jayachandran et al., “Synthesis, Characterization, and Utility of Trialkyl(3-sulfopropyl)ammonium Betaines as New Phase Transfer Reagents,”Synthetic Communications, (2003), vol. 33, No. 14, pp. 2463 to 2468.
Gerhard Quinkert et al., “120.Stereoselective Ring Opening of Electronically Excited cyclohexa-2,4-dienones: Cause and Effect,”Helvetica Chimica Acta, vol. 80, (1997) pp. 1683 to 1772.
English-language International Preliminary Report on Patentability and Written Opinion of the International Searching Authority, dated Feb. 26, 2008 for International application PCT/JP2006/306806 filed Mar. 31, 2006; Applicants: Sankyo Agro Company, Limited.

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