Hydrochloric Acid → HCID 10882462, compound

Participants

Reaction Conditions

Reaction Steps

2-(4-Hydroxyphenoxy)propionic acid (2.85 gm, 0.0156 mole) was dissolved in 60 ml of dimethylsulfoxide. A solution of sodium hydroxide (1.25 gm, 0.031 mole) in 2.0 ml of water was added and the mixture stirred for a few minutes to insure complete conversion to the disodium salt. 2,6-Dichloroquinoline (3.1 gm, 0.0126 mole) was dissolved in 50 ml of DMSO and then added all at once to the sodium phenate solution. The reaction mixture was then heated to about 125° C. and stirred at this temperature for 3.0 hours. At the end of this time it was cooled, poured into 350 ml of cold water and acidified with concentrated hydrochloric acid. The precipitated crude product was collected on a filter, washed with fresh water, sucked damp dry and taken up in hot toluene. It was then dried over sodium sulfate, treated with "Norite", filtered and the filtrate concentrated and chilled to precipitate the white crystalline 2-(4-((6-chloro-2-quinolinyl)oxy)phenoxy)propionic acid.

Provenance & Evidence