Ethylene Glycol → 2-(4-Chlorophenyl)butanoic acid

Participants

Reaction Steps

A 5-liter, 3-neck flask is charged with 400 g (1.9 moles) of (I), 350 g potassium hydroxide, 2.47 liters of ethylene glycol and 155 g of 95% hydrazine diluted to 250 ml with water. The mixture is refluxed for 1.5 hours, after which the water is drained from the condenser and the internal temperature of the reaction mixture is allowed to rise to 190°. Refluxing is then continued for another 4 hours. The cooled solution is diluted with 2.5 liters of water and poured slowly into 2.0 liters of 6N hydrochloric acid. The precipitate is filtered and air-dried. Yield: 332.5 g, 88.1%, mp 54°-57°.

Provenance & Evidence