Hydroquinone → 2-Cyclopenten-1-one, 4-hydroxy-3-methyl-2-(2-propen-1-yl)-

Participants

Reaction Steps

Three hundred milligrams of a furan compound of the formula (II) (R1 =CH3, R2 =--CH2 --CH=CH2, R3 =CH3) was added to a dioxane/water mixture (dioxane 3.0 ml, water 2.0 ml), and then hydroquinone (10 mg) was added thereto. To the solution was added a phosphate buffer solution [a solution of potassium dihydrogen phosphate (0.27 g) and sodium monohydrogen phosphate (0.36 g) in water (5.0 ml)], followed by refluxing for 90 minutes. After adding water (10 ml) to the reaction solution, the solution was saturated with sodium chloride and extracted twice with ether. The ether layer was dried over magnesium sulfate, and the solvent was removed by evaporation. By column chromatography on silica gel, 135 mg of allethrolone (2-methyl-3-allyl-cyclopent-2-en-4-on-1-ol) was obtained.

Provenance & Evidence