Isopropanol → 3-(2,4-Dichlorophenoxy)propanoic acid

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Reaction Steps

Jones reagent (2.3M, 0.283 L, 0.650 mol, CrO3 /H2SO4) is added to a solution of 3-(2,4-dichlorophenoxy)-1-propanol (71.87 g, 0.325 mol) in acetone while maintaining the temperature of the reaction mixture below 40° C. After the addition is complete, isopropanol is added and the reaction mixture is filtered through diatomaceous earth. The filtrate is concentrated in vacuo to give a blue-green solid which is partitioned between ether and water. The organic phase is separated, washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo to obtain the title product as a yellow solid (69.87 g, mp 93°-95° C.).

Provenance & Evidence