Ethylene Glycol → 2-(1,1-Dimethylethyl)-2-(4-carboxyphenyl)-1,3-dioxolane

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Reaction Steps

A mixture of 63.5 grams (0.31 mole) of 4-(2,2-dimethyl-1-oxopropyl)benzoic acid, 156 ml. of ethylene glycol, and 1 gram of toluenesulfonic acid in 600 ml of toluene is refluxed for 24 hours using a Dean-Stark trap to remove water. The mixture is then cooled and partially evaporated; and to the residue, 4.5 grams of solid potassium hydroxide are carefully added followed by 225 ml of water. The resulting mixture is refluxed for 11/2 hours, cooled, filtered and the layers separated. The aqueous layer is acidified with 2N hydrochloric acid, and the resulting precipitate is removed by filtration. The precipitate is washed with water, then water/ethanol (5/1), and then petroleum ether. The product is dried in vacuo to yield the title product (m.p. 213.5°-215.5° C.).

Provenance & Evidence