Acetoacetylation with 2,2,6-Trimethyl-4H-1,3-dioxin-4-one: A Convenient Alternative to Diketene

Journal of Organic Chemistry

Volumn 50, Issue 14, 1985, Pages 2431-2435

  Clemens, Robert J ^a   Hyatt, John A ^a  

^a EASTMAN KODAK COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000392068     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00214a006     Document Type: Article

References (11)

1. For acetoacetylation procedures using diketene, see: Wilson, S. R.; Price, M F. J. Org. Chem. 1984, 49, 722 and ref 14 there in.
2. An effective, but more expensive, alternative to diketene is 5-acetyl
3. Carroll, M. F.; Bader, A. R. J. Am. Chem. Soc. 1952, 74, 6306. See also: Carroll, M. F.; Bader, A. R. J. Am. Chem. Soc. 1953, 75, 5400.
4. Bader, A. R.; Cummings, L. O.; Vogel, H. A. J. Am. Chem. Soc. 1951, 73, 4195–4197.
5. Sato, M.; Kanuwa, N.; Kato, T. Chem. Pharm. Bull. 1982, 30, 1315.
6. Available from Kodak Laboratory Chemicals and Aldrich Chemical Co.
7. Other nonnucleophilic, nonketonic solvents can also be used. (9) Phenyl thioacetoacetate is reported to decompose upon attempted distillation: Yaggi, N. F.; Douglas, K. T. J. Chem. Soc., Chem. Commun. 1977, 609.
8. Booth, P. M.; Fox, C. M. J.; Ley, S. V. Tetrahedron Lett. 1983, 24, 5143–5146.
9. Kellogg, R. M.; Van Bergen, T. J.; Van Doren, H.; Hedstrand, D.; Kooi, J.; Kruizinga, W. H.; Troostwijik, C. B. J. Org. Chem. 1980, 45, 2854–2861 and ref 25 there in. We note a discrepancy between the shift values of the NMR spectrum they have reported (acetyl methyl protons atδ 2.88) and ours (δ 2.36).
10. Heckles, J. S. (Armstrong). U.S. Patent 4 217 396, 1980; Chem. Abstr. 1980, 93, 222047.
11. Rail, K. B.; Perekalin, V. V. J. Gen. Chem. USSR (Engl. Transl.) 1955, 25, 259; Synthesis 1976, 680.