Hydrochloric Acid → 4-Pentyl-3-cyclohexenylcarboxylic acid

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Reaction Steps

Ethyl 4-pentyl-3-cyclohexen-l-carboxylate (3.0 g) is added to a solution of water (27 ml) and potassium hydroxide (2.6 g). The mixture is stirred under reflux for 16 hours. The reaction mixture is then neutralized with a mixture of concentrated HCl (40 ml), water (40 ml), and ice (ca. 40 g), and the mixture extracted with dichloromethane (100 ml). The combined organic extracts are dried with sodium sulfate, and the solution concentrated in vacuo. The solid is recrystallized from a mixture of methanol (70 ml) and water (25 ml), resulting in the product, 4-pentyl-3-cyclohexen-1-carboxylic acid.

Provenance & Evidence