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After ten hours of refluxing 250 cc. of water was added, the alcohol distilled off, and the residual solution treated with 275 cc. of concentrated hydrochloric acid with stirring and external cooling. The reaction mixture, now acid to congo red, was extracted with five 200-cc. portions of ether. The combined ethereal extracts were washed with saturated salt solution, dried over sodium sulfate and the ether distilled. The resulting crude dicarboxylic acid weighed 157 g. which was recrystallized from benzene-petroleum ether, giving 136 g. of a white crystalline product melting a t 105-106.5" in a yield of 85%. This was decarboxylated by heating at 190-200 a for five hours and then fractionated i n vucuo, giving 61.2 g. of a-allylcyclobutanepropionic acid, b. p . 142--150" at 17 mm., in a yield of 85.870.Anal. Calcd. for CIOH1eOZ: C, 71.39; H , 9.58. Found: C, 71.09; H, 9.33. This acid was converted to the acid chloride by means of phosphorus trichloride, as above, and fractionated in vucuo, giving a 70.5% yield of a-allylcyclobutanepropionyl chloride, b. p. 90-95" a t 13 mm. Subsequently, improved yields were obtained by chlorinating with thionyl chloride : 31 g. of the acid and 33 g. of thionyl chloride were mixed and heated on a water-bath maintained a t 40-50 "for thirty minutes and then refluxed for three hours. The thionyl chloride was removed and the residue fractionated yielding 28.7 g. of the desired acid chloride, b. p . 95-99' a t 14 mm. in a yield of 83.5%.Anal. Calcd. for CloH&lO: C1, 19.03. Found: C1, 18.59.To prepare the ureide, the acid chloride and urea in molar proportions of 1:4 were mixed in the absence of

The rearrangement undoubtedly takes place through an intermediate O-acetyl base, and is much more rapid in the T-ephedrine derivative than in the one having the configuration of ephedrifie. The speed of rearrangement is affected by the hydrogen ion concentration, and is practically instantaneous at a sufficiently high pH.