Chromium(VI) Oxide-Quinoline

(CrO3)

[1333-82-0]  · CrO3  · Chromium(VI) Oxide-Quinoline  · (MW 99.99) (quinoline)

[91-22-5]  · C9H7N  · Chromium(VI) Oxide-Quinoline  · (MW 129.16)

(mild selective reagent for the oxidation of primary and secondary alcohols to the corresponding carbonyl compounds under basic conditions)

Preparative Methods: the reagent is prepared either in solid solid form prior to use or in situ in excess base in the presence of the alcohol.1

Handling, Storage, and Precautions: caution all chromium(VI) reagents must be handled with care. The mutagenicity of chromium(VI) compounds is well documented.2 This reagent should be handled in a fume hood.

General Considerations.

Chromium(VI) oxide reacts with organic bases such as isoquinoline, lutidines, picolines, pyridine, and quinoline to give 1:2 (oxide:base) complexes which are useful for oxidizing primary and secondary alcohols to the corresponding carbonyl compounds.1,3-5 Other chromium reagents for oxidizing primary and secondary alcohols to carbonyl compounds under basic conditions include Dipyridine Chromium(VI) Oxide,1,3 chromium(VI) oxide-triethylamine,1 Chromium(VI) Oxide-3,5-Dimethylpyrazole, Collins' and Ratcliffe's reagents (see Dipyridine Chromium(VI) Oxide), and Pyridinium Chlorochromate.6,7

Oxidation of Hydrocortisone Acetate to Cortisone Acetate.

Hydrocortisone acetate (21-acetoxy-11b,17a-dihydroxy-4-pregnene-3,20-dione) reacts with chromium(VI) oxide-quinoline to yield cortisone acetate (eq 1).1


1. Merck & Co. Br. Patent 733 808, 1955 (CA 1956, 50, 16 882).
2. Cupo, D. Y.; Wetterhahn, K. E. Cancer Res. 1985, 45, 1146.
3. Poos, G. I.; Arth, G. E.; Beyler, R. E.; Sarett, L. H. JACS 1953, 75, 422.
4. Sisler, H. H.; Bush, J. D.; Accountius, O. E. JACS 1948, 70, 3827.
5. Sisler, H. H.; Ming, W. C. L.; Metter, E.; Hurley, F. R. JACS 1953, 75, 446.
6. Guziec, Jr., F. S.; Luzzio, F. A. JOC 1982, 47, 1787.
7. Guziec, Jr., F. S.; Luzzio, F. A. OPP 1988, 20, 533.

Fillmore Freeman

University of California, Irvine, CA, USA



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