as that described was heated three-quarters of an hour and then poured into 200 ml. of water.Sodium bicarbonate was added to excess.After reaction ceased, the solution was extracted twice with chloroform and the combined, dried extracts were concentrated under reduced pressure to a residual oil which was dissolved without delay in about 70-100 ml. of water and assayed spectrophotometrically. Under the conditions described, 30% was a typical yield. Addition of a few crystals of hydroquinone is advisable. Solutions without antioxidant deposit anemonin in various degrees of purity quite rapidly. The mixed m. p. of a purified sample with anemonin from natural protanemonin was not depressed.Variations in the amount of sulfuric acid used affected the rate at which the maximum yield of protoanemonin was reached, but not the yield itself. The conversion of acetylacrylic acid to protoanemonin was also achieved in solvents other than acetic acid, such as dioxane (peroxide-free), and with other catalysts, such as ^-toluene sulfonic acid.3-Bromopentene-2-olide-l,4 (VII).-The attempted dehydrobromination of the bromoacetoxy lactone (VI) with anhydrous sodium acetate in dry ether3 gave a neutral fraction which, even after fifteen hours of reflux, contained a very high bromine content.Fractionation gave material b. p. 60-64°(1 mm.) which crystallized in a Dry Ice-alcohol-bath. Rapid filtration left a colorless solid, m.p. 49-53°, which, after recrystallization from ethyl acetate, reached a constant m. p. 51-53°.
The thermal decomposition of benzene in quartz is, under the conditions investigated, a heterogeneous, bimolecular reaction that is strongly retarded by the adsorption of products on the surface of the reaction vessel. Steel also catalyzes the reaction.The plot of log k vs. 1/T gives a straight line whose slope corresponds to an apparent energy of activation of 50,000 calories.
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