Title:
PROCESS FOR PRODUCING THIOCARBOXYLIC ACID OR SALT THEREOF, METHOD OF DETERMINING OPTICAL PURITY OF THESE, AND TETRAHYDROFURANTHIOCARBOXYLIC ACID OR DERIVATIVE THEREOF
Document Type and Number:
WIPO Patent Application WO/2003/037855
Kind Code:
A1
Abstract:
A high−purity thiocarboxylic acid or a salt thereof can be obtained by: reacting an acid halide or acid anhydride with a metal salt of hydrogen sulfide in the presence of a base&semi and&sol or adding an organic solvent having a relative permittivity at 20°C of 4.0 or lower to a mixture of a thiocarboxylic acid, the corresponding carboxylic acid, and water and extracting the thiocarboxylic acid selectively into the organic solvent&semi and&sol or adding a base to a mixture of a thiocarboxylic acid and the corresponding carboxylic acid and conducting crystallization&sol separation by filtration. This method is especially suitable when the thiocarboxylic acid is tetrahydrofuranthiocarboxylic acid. An optically active tetrahydrofuranthiocarboxylic acid is converted to an alkyl ester and this ester is analyzed by chromatography with an optically active column. Thus, the optical purity of the optically active tetrahydrofuranthiocarboxylic acid can be determined with satisfactory precision.
Inventors:
ISHIKAWA MAMORU (JP)
NISHIMURA KAZUAKI (JP)
NISHIMURA KAZUAKI (JP)
Application Number:
PCT/JP2002/011342
Publication Date:
May 08, 2003
Filing Date:
October 31, 2002
Export Citation:
Assignee:
TORAY INDUSTRIES (JP)
ISHIKAWA MAMORU (JP)
NISHIMURA KAZUAKI (JP)
ISHIKAWA MAMORU (JP)
NISHIMURA KAZUAKI (JP)
International Classes:
C07C327/02; (IPC1-7): C07C327/06; C07C327/16; C07D307/24
Foreign References:
| US4233060A | 1980-11-11 | |||
| US4000173A | 1976-12-28 | |||
| EP0563878A2 | 1993-10-06 | |||
| JPH05249093A | 1993-09-28 |
Other References:
1962, KYORITSU SHUPPAN CO. LTD., article "Kagaku daijiten 5", pages: 809, XP002963748
SKURKO M.R. ET AL.: "Proton acceptor properties of carbonyl-containing derivatives of tetrahydro-2-furoic acid", IZVESTIYA AKADEMII NAUK SSSR, SERIYA KHIMICHESKAYA, vol. 9, 1982, pages 2034 - 2037, XP002963749
KHUMTAVEEPORN KANJAI ET AL.: "Regioselective carbonyl insertion reactions with alpha-substituted heterocycles", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, vol. 9, 1995, pages 917 - 918, XP002963750
BARRETT ANTHONY G.M. ET AL.: "Stereoselective syntheses of S-phenyl tetrahydrofuran-2-thiocarboxylate and tetrahydropyran-2-thiocarboxylate derivatives using (phenylthio) nitromethane", JOURNAL OF ORGANIC CHEMISTRY, vol. 54, no. 19, 1989, pages 4723 - 4726, XP002963751
SKURKO M.R. ET AL.: "Proton acceptor properties of carbonyl-containing derivatives of tetrahydro-2-furoic acid", IZVESTIYA AKADEMII NAUK SSSR, SERIYA KHIMICHESKAYA, vol. 9, 1982, pages 2034 - 2037, XP002963749
KHUMTAVEEPORN KANJAI ET AL.: "Regioselective carbonyl insertion reactions with alpha-substituted heterocycles", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, vol. 9, 1995, pages 917 - 918, XP002963750
BARRETT ANTHONY G.M. ET AL.: "Stereoselective syntheses of S-phenyl tetrahydrofuran-2-thiocarboxylate and tetrahydropyran-2-thiocarboxylate derivatives using (phenylthio) nitromethane", JOURNAL OF ORGANIC CHEMISTRY, vol. 54, no. 19, 1989, pages 4723 - 4726, XP002963751
Attorney, Agent or Firm:
Sato, Kenji c/o Shiga, Branch (TORAY INTELLECTUAL PROPERTY EXPERTS CO. LTD. 1-, Sonoyama 1-chome Otsu-shi Shiga, JP)
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