Process for the production of tetronic acid

Details Process for the production of tetronic acid Process for the production of tetronic acid

1982-06-14

1983-12-20

Milestone, Norma S.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D30760

Patent

active

044219229

ABSTRACT:
Process for the production of tetronic acid from 4-haloacetoacetic ester which begins by converting a 4-haloacetoacetic ester into the corresponding 4-benzyloxyacetoacetic ester. The 4-benzyl ester is then hydrogenolyzed into an intermediate product. The 4-hydroxyacetoacetic ester is converted by treatment with acid into tetronic acid. The 4-hydroxyacetoacetic ester can be isolated before conversion. The 4-benzyloxyacetoacetic ester can be produced by conversion of the 4-haloacetoacetic ester with a metal salt of benzyl alcohol. The hydrogenolysis can be carried out in the presence of an acid, whereby the 4-hydroxyacetoacetic ester forming in situ is rearranged directly into tetronic acid. The hydrogenolysis can be carried out under pressure in the presence of a hydrogenation catalyst.

REFERENCES:
patent: Re28242 (1974-11-01), Boosen
patent: 3210377 (1965-10-01), Machleidt
patent: 3824255 (1974-07-01), Boosen
"The Total Synthesis of the Antibiotic Malonomicin", Tetrahedron, vol. 34, (1978), pp. 223 to 231, by Baan et al.

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