Lactones

Details Lactones Lactones

1976-07-06

1982-01-12

Milestone, Norma S.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260544Y, 560124, 560226, 560228, C07D30732

Patent

active

043104649

ABSTRACT:
4-.beta., .beta.-dichlorovinyl (or dibromovinyl)-3,3-dimethylbutyrolactones are prepared from 1,1-dichloro (or dibromo)-4-methylpenta-1,3-diene by reacting with an acid of formula CH.sub.2 R.CO.sub.2 H in presence of a salt of a metal in one of its higher valency states, especially manganese (III), cerium (IV), or vanadium (V). Higher yields are obtained in the presence of the anhydride of the acid and of the sodium or potassium salt of the acid. Treatment of the lactones with an inorganic acid halide opens the lactone ring with formation of the corresponding 4-haloacid halide, which with alcohols affords the corresponding 4-haloacid ester, cyclised by bases to a 3-.beta.,.beta.-dichloro (or dibromo)vinyl-2,2-dimethylcyclopropanecarboxylic ester, intermediate for insecticides such as the m-phenoxybenzyl ester.

REFERENCES:
patent: 3488732 (1970-01-01), Heiba et al.
patent: 3758514 (1973-09-01), Heiba et al.
patent: 3813416 (1974-05-01), Heiba et al.
Finkbeiner et al., Ox. of Acetic Acid by Mn.sup.+3 Salts (8-68).
Heiba et al., J.A.C.S. 96: 26, pp. 7977-7981 (1974).
Finkbeiner et al., C.A. 72: 89803w (1970).

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