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CARBOHYDRATE OXIDATION. I 3085 the solution filtered. The filtrate was cooled to 0°and very carefully neutralized with cold hydrochloric acid. The crystalline material so obtained was rapidly filtered off and washed several times with ice water; yield, 60%. The product was purified by crystallization from alcohol or preferably from benzene.Four g. of ethyl-vinyloxyethyl-barbituric acid, prepared as described above, was placed in 30 cc. of hot water, in which it is insoluble. On the addition of 2 cc. of hydrochloric acid and stirring, the solid dissolved almost immediately while the acetaldehyde formed by the hydrolysis was removed by boiling. The product crystallized on cooling and was purified by crystallization either from alcohol or water; yield of ethyl-d-hydroxyethyl-barbituric acid, 70%. Summary 1. A method for the preparation of hydroxy-substituted alkyl-barbituric acids has been described.2. The compounds so prepared may be hypnotics with properties similar to those of veronal and proponal, and should be less toxic. The result of a study of their pharmacology will be reported later.

The parachor, P, as derived by Sugden, has been stated in the form d My\ D-d' where M is the molecular weight, 7 the surface tension, and D and d are the densities of the liquid and vapor respectively at the same temperature.The CHt group.*-By applying the above formula to hundreds of organic compounds and fixing, as a standard for comparison, the covalent bond at zero, Sugden1 arrived at an average value of 39.0 for the CH2 group. This value has been the subject of much discussion ever since. Mumford and Phillips2, from a study of high-molecular-weight compounds, concluded that the CH2 group should be given a value of 40.0, Vogel3, from parachor determinations on the methyl and ethyl esters of n-dibasic acids, obtained 40.3, and Desreux4, from the higher members of the paraffin and normal alkyl fluoride and chloride series, found values which varied but slightly from 39.9. More recently Sugden6 has been inclined to accept the value of 39.6 for the CH2 group.These variations at once detract from the usefulness of the parachor in any quantitative approach to the determination of structure. Although the differences were at first thought to be due to impurities or inaccurate measurements, it now appears that they are of a more fundamental nature. As Desreux pointed out, they doubtless indicate that the atomic parachors are not strictly additive. In fact the CH2 values of Desreux for the paraffins and alkyl fluorides and chlorides are unique in their constancy.* Shortly after the submission of this manuscript Bayliss, J. Am. Chem. Soc., 69, 444 (1937), by the method of least squares, found the CHi value to be 39.92.