The rearrangement of fatty epoxyesters to ketoesters was studied. The isomerization is carried out in nonaqueous media and is catalyzed by acids. Esters containing one epoxy group per fatty acid chain are isomerized to the corresponding ketones in 70舑90% yields using boron fluoride etherate catalyst in boiling dioxane. Conversion to ketonic products is measured either by chromatographic separation followed by IR analysis or by oximation. Principal byproducts are hydroxy derivatives. Fatty esters containing more than one epoxy group/fatty acid chain give low ketone yields.

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To 15 ml. of diethylaniline, 1.91 g. of 3,4-bis(4-allyloxyphenyl)-3,4-hexanediol (lib) was added and the solution refluxed under nitrogen for 6 hr. The reaction mixture was poured into 200 ml. of 2iV hydrochloric acid, stirred, and then extracted with ether. The ether extract was washed with water, dried over sodium sulfate, and the solvent evaporated. The residue, a viscous oil, was used without further purification for dehydration to 3,3 '-diallyldienestrol diacetate. The dehydration was carried out by refluxing the oil, meso-3,4-bis(3-allyl-4-hydroxyphenyl)-3,4-hexanediol, with a mixture of 10 ml. of acetyl chloride and 10 ml. of acetic anhydride for 4 hr. Four hundred milliliters of water was added and the mixture extracted with ether. The ether extract was washed with a sodium bicarbonate solution, then with water, dried over sodium sulfate, and the ether evaporated. The residue was crystallized from ethanol and then recrystallized from an ether-petroleum ether (b.p. 40-60°) mixture. The 3,3'diallyldienestrol diacetate melted at 145-147°and its yield was 0.25 g.

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