COUMARINS FROM ORCINOL DERIVATIVES: CONDENSATION OF ORCACETOPHENONE MONOMETHYL ETHER WITH ETHYL ACETATE, ETHYL PROPIONATE AND ETHYL BUTYRATE, AND MOLECULAR REARRANGEMENT OF ORCACETOPHENONE DIACETATE AND DIBENZOATE, IN PRESENCE OF METALLIC SODIUM
| Main Authors: | SHARAD S. PANDIT, SURESH SETHNA |
|---|---|
| Format: | Article Journal |
| Bahasa: | eng |
| Terbitan: |
, 1951
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| Subjects: | |
| Online Access: |
https://zenodo.org/record/6565356 |
Daftar Isi:
- Orcacetophcnone monomethyl ether has been condensed with ethyl acetate, ethyl propionate and ethyl butyrate in presence of metallic sodium.; instead of the expected \(\beta\)-diketones other products are obtained to which the structures of 4-hydroxy-7-methoxy-4 :5-dimethyl-, -3 :4:5-trimethyl-, and -3-ethyl-4 :5-dimethyl-3 :4-dihydrocoumarin respectively, have been tentatively assigned. Molecular rearrangement of orcacetophenone diacetate in presence of metallic sodium gives 7-hydroxy-4-acetomethyl-5-methylconmarin instead of the isomeric chromone. The formation of coumarin derivatives in the above reactions has not been observed before. Similar rearrangement of orcacetophenone dibenzoate gives the expected 7-hydroxy-5-methylflavone.