Patent · US Expired

1-(2-Substituted-chromonyloxy)-2-hydroxy-3-(substituted phenoxy)propanes

US3953604A · kind A · utility

10Cited by
4References
2Claims
0Family size

Assignee

Inventors

Key dates

Filing dateDec 3, 1973
Grant dateApr 27, 1976
Priority date
Expiry dateDec 3, 1993

Classification

  • Technology area (CPC C)Chemistry; Metallurgy
  • CPC primaryC07C205/37
  • WIPO fieldOrganic fine chemistry
  • WIPO sectorChemistry

Abstract

Definitions: in the following Formulae I, II and IV, R.sup.1 represents hydrogen, alkyl of 1 to 4 carbon atoms, or a nontoxic cation, while each of R.sup.2, R.sup.3, R.sup.4, R.sup.5, and R.sup.6 symbolizes hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, carboxy, carbalkoxy of 1 to 4 carbon atoms, trihalomethyl, halogen, nitro or cyano. Certain 1-(2-substituted-chromon-yloxy)-2-hydroxy-3-(substituted-phenoxy)propanes (Formula I), ##SPC1## can be synthesized from intermediate bis-(substituted-phenoxy)propanes (Formula II), ##SPC2## by condensation with diethyl oxalate in the presence of sodium ethoxide followed by cyclization with a mixture of glacial acetic acid and concentrated sulfuric or a mixture of concentrated hydrochloric acid and a lower alcohol containing up to 4 carbon atoms. The bis-(substituted-phenoxy)propane intermediates (Formula II) are prepared by reacting a dihydroxyacetophenone (Formula III), ##SPC3## with a (substituted-phenyl)glycidyl ether (Formula IV), ##SPC4## in an organic solvent in the presence of a catalyst. The 1-(2-substituted-chromon-yloxy)-2-hydroxy-3-(substituted-phenoxy)propanes (Formula I) are useful in the treatment of alle…

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