Organic compounds -- part of the class 532-570 series – Organic compounds – Sulfonate esters
Patent
1993-01-15
1993-12-28
Evans, Joseph E.
Organic compounds -- part of the class 532-570 series
Organic compounds
Sulfonate esters
549511, 549556, C07D30100, C07D30132, C07D30316
Patent
active
052741605
ABSTRACT:
There is disclosed a process for producing an alkyl casylate by the reaction of a metal casylate or an enantiomer of a quaternary casylate with a trialkyl phosphite in the presence of a slight molar excess of sulfuric acid. According to one aspect of the invention the reaction is conducted under heat in the presence of concentrated sulfuric acid. When the reaction is complete, an organic layer that contains the alkyl casylate is isolated. In another aspect of the invention at least 1.0 equivalents of a trialkyl phosphite is added to a thoroughly dried enantiomer of camphorsulfonic acid, and the mixture optionally heated to about 80.degree. C. The reaction is allowed to proceed until camphorsulfonic acid is no longer present. Thereafter all phosphorus-containing species are selectively removed by distillation at reduced pressure to obtain a pure alkyl casylate in high yield.
REFERENCES:
patent: 2669574 (1954-02-01), Thompson
patent: 3053855 (1962-09-01), Maerker et al.
patent: 3859314 (1975-01-01), Dukes et al.
patent: 3956354 (1976-05-01), Schroeck
patent: 4395542 (1983-07-01), Sury
patent: 4540769 (1985-09-01), Dobinson et al.
patent: 4810808 (1989-03-01), Tomita et al.
patent: 4831101 (1989-05-01), Jellinek et al.
patent: 4931576 (1990-06-01), Wirth et al.
Advertisement, Aldrich Chemical Co. J. Org. Chem., vol. 55, #19 (1990).
Aitken, Royer, and Husson, J. Org. Chem. 55:2814-2820 (1990).
Guivisdalsky, and Bittman, J. Org. Chem. 54:4643-4648 (1989).
Byun, and Bittman, Tetrahedron Letters, vol. 30, #21:2751-2754 (1989).
Hahn and Tompkins, J. Org. Chem. 53:5783-5785 (1988).
Klunder, Tetsue and Sharpless, J. Org. Chem. 54:1295-1304 (1989).
Nitta, Arakawa and Naoto, Chem. Pharm. Bull. 34:2710 (1986).
Najdi, Reichlin and Kurth, J. Org. Chem. 55:6241-6244 (1989).
Jurczak, Pikul, and Bauer, T. Tetrahedron 42.2:447-450 (1986).
Evans Joseph E.
Syracuse University
LandOfFree
Method and apparatus for synthesis of highly isomerically pure s does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Method and apparatus for synthesis of highly isomerically pure s, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method and apparatus for synthesis of highly isomerically pure s will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1544360