Quinoline → 5-(2-Formyl-3-hydroxyphenoxy)pentanoic acid

Participants

Reaction Steps

5-(2-Formyl-3-hydroxy-4-carboxyphenoxy)pentanoic acid (Example 6) (0.2 g, 0.0007 M), copper (0.05 g) and quinoline (5 ml) were heated at 210° C. for 1/2 hour. The reaction mixture was cooled and filtered. Ether (20 ml) was added to the filtrate and the organic layer was washed with 2 N hydrochloric acid (3×20 ml), water (1×20 ml) and brine (1×20 ml), dried (magnesium sulphate) and the solvent removed in vacuo to give 5-(2-formyl-3-hydroxyphenoxy)pentanoic acid as a pale-yellow oil that solidified on standing and was homogeneous on thin layer chromatography (silicagel plates; chloroform:methanol, 10:1).

Provenance & Evidence