Alkyl aryl sulfones and method of preparing the same

Details Alkyl aryl sulfones and method of preparing the same Alkyl aryl sulfones and method of preparing the same

1988-03-31

1991-05-14

Ceperley, Mary E.

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

Organic compounds

Sulfur containing

568 29, 568 31, 568 33, 568 34, 568 35, C07C31500

Patent

active

050157752

ABSTRACT:
Alkyl aryl sulfones of the formula R--SO.sub.2 --AR--Y.sub.n, wherein Ar is an aryl compound, Y is a substituent on the aryl compound and R is alkyl or cycloalkyl, and liquid mixtures of positional isomers of the same are prepared by reacting an aryl compound of the formula Ar--Y.sub.n, with an alkyl sulfonic acid of the formula R--SO.sub.3 H and a phosphorus reagent, preferably under heat. Particularly good yields and pure products are obtained using phosphorus pentoxide. Alkyl aryl sulfones produced by this method are a liquid mixture preferably containing at least two positional isomers, wherein no isomer is present in an amount of more than about 50% of the isomer mixture.

REFERENCES:
patent: 3125604 (1964-03-01), Robbins
patent: 3250812 (1966-05-01), Gilbert
patent: 3501532 (1970-03-01), Minor et al.
patent: 3579590 (1971-05-01), Davis
patent: 4386221 (1983-05-01), Hyatt et al.
M. Grant et al., J. Chem. Soc., p. 2520 (1959).
C. Suter, The Organic Chemistry of Sulfur, pp. 676-677 (1944), John Wiley and Sons, Inc., N.Y.
Organische Schwefel-Verbindungen, p. 1165 (1985), Georg Thieme Verlag Publishers, N.Y.
EPO Search Report for Application No. 89102131.3, corresponding to this U.S. application.
E. E. Gilbert, "A New Synthesis of Methyl Aryl Sulfones", J. Org. Chem., 28:1945 (1963).
J. A. Hyatt et al., "Synthesis of Aryl Alkyl and Aryl Vinyl Sulfones via Friedel-Crafts Reactions of Sulfonyl Fluorides", Synthesis, 214-217 (1984).
W. E. Truce et al., "Friedel-Crafts Reactions of Methanesulfonyl Chloride with Benzene and Certain Substituted Benzenes", J. Amer. Chem. Soc., 5032 (1953).
P. Oxley et al., "Amidines. Part II. Preparation of Cyanides, Amides, and Amidines from Carboxylic Acids", J. Chem. Soc., 763-771 (1946).
Suter, C., "Tetracovalent Sulfur Compounds", The Organic Chemistry of Sulfur, pp. 673-679 plus References p. 762 (1944).
Premasagar, V. et al., "Methanesulfonic Acid Catalyzed Cyclization of 3-Arylpropanoic and 4-Arylbutanoic Acids to 1-Indanones and 1-Tetralones", J. Org. Chem., pp. 2974-2976, vol. 46, No. 14, 1981.
Eaton, P. et al., "Phosphorus Pentoxide-Methanesulfonic Acid. A Convenient Alternative to Polyphosphoric Acid", J. Org. Chem., vol. 38, No. 23, 1973.
Ueda, M. et al., "A New Synthesis of Diaryl Sulfones", Synthesis, pp. 323-325 (Apr. 1984).
Meyer, von Hans, "Zur Kenntnis der Aromatischen Sulfosauren und Sulfone", Annalen der Chemie, 433, pp. 327-350 (1923).
Ueda, M. et al., "Synthesis of Aromatic Poly(Ether Ketones)", Macromolecules, 20, pp. 2675-2678 (1987).
Bodine, R. et al., "C-Labeled Benzo[a]Pyrene and Derivatives. 1. Efficient Pathways to Labeling the 4,5,11, and 12 Positions", J. Org. Chem., vol. 43, No. 21 (1978).
Kuczynski, H. et al., "O Sulfokwasach Sulfonow Aromatycznych", Rocznikl Chemll., T. XVII, 18, pp. 625-650 (1938), and Chemical Abstract, p. 1940, Col. 3246.
Michael, A. et al., "Zur Kenntniss der Aromatischen Sulfone", pp. 583-587.
Truce, W. et al., "Aromatic Sulonylation", Sulfones and Sulfoximines, pp. 532-536, 597.

Affiliated with

Also associated with

Rating

Alkyl aryl sulfones and method of preparing the same does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Alkyl aryl sulfones and method of preparing the same, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Alkyl aryl sulfones and method of preparing the same will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1649598