iiig with 150 ml. of cold water and t w o 5O-iii1. portions of 5% sodium carbonate, the ether solution was dried with sodium sulfate and evaporated to a red oil; yield 16.3 g . (YOc;;). Distillation a t 0.2 mm. gave 2.4-g. forerun boilIn principle one could further elucidate the de- ing below 87" aFd 10.3 g. (57%) of chloroketone distilling tailed molecular structure by either a theoretical bet ween 87-92 Two recrystallizations from petroleum calculation of the expected magnetic susceptibility cther gave colorless iicedles, m. p . 60". The compound ior each of the various models or through a coni- recrystallized immediately after ineltiiig aiid rcincltctl at parison with the appropriate experimental values. 54". A n d 2 Calcd. for CloH1102C1:C, 60.46; €1, 5 Actually neither method is sufficiently refined to Found: C, 60.61; €I, 6.71. distinguish between the various structural possi$-(Z-Methyl-4-nitrophenoxy) -lactic Acid.-Ten grain,\ bilities. Using the method of Angus3one can sum of p-chlorolactic acid, 24.6 g. of 2-methyl-4-nitropheiiol the appropriate values of t 4 iodine and - 2 oxy- arid 86 ml. of 12Oh sodium hydroxide were heated two for LO4. hours on the steam-bath. The cooled aqueous solution gen to obtain a value of -96.52 X was acidified to congo red and extracted with ether. The Alternately, assuming a structure of (IO+) (108-) substituted lactic acid separated on acidification of a and using Angus' values of +3 and +5 iodine, potassium bicarbonate extract of the ether solution. Rcone calculates -97.10 X lo+. These discrep- crystallization from hot water, after treatment with Darco ancies are not unexpected and indeed are no G-60 gave 3.27 g. (17%) of a pale yellow powder, conby a few bright yellow needles which werc larger than might be anticipated for such a calru- taminated separated manually. The major product melted at 11 1' lation. Summation of Pascal's4 experimental after recrystallization from water. v:ilucs leads to -107.64 X here again one A d . Calcd. for C , O H ~ ~ O &C, : 49.79; H, 4.60. iiiight expect too large a value since Pascal's value Pound: C, 49.51; H, 4.48. The minor product, in. p. 85",after recrystallization for iodine is applicable to a single bonded covalent iodide atom. An experimental value5 of 1 0 3 - of from water, was not further characterized. o-Toloxyacetylglycine.-Five ml. of o-toloxyacetyl chlo-51.4 X would lead, on the assumption of ride (b.p. 108-109" (8 mm.)) was added with stirring and the iodyl iodate model, to an experimental valuc cooling to 13.3 g. of glycine homogenized with 13 ml. of 20%) sodium hydroxide. LVhen the reaction had subsided, of -24.88 X 10" for the iodyl ion. slternate additions of 1 3 ml. of sodium hydroxide and 5 ml. Acknowledgment.--%-e are indebted to the of the acid chloride were made until a total of 32.7 g. of the Office of Naval Research for financial support of acid chloride and 76 nil. of sodium hydroxide had been added. After standing an hour and a half, the reactants this work. were poured into chipped ice, acidified to congo red with (3) Angus, Proc Roy SOL i l o n d o n ) , A136, 5Scl ( 1 9 3 L j dilute hydrochloric acid and filtered. The crude product (4) Selwood, "Erfagnetochennstry," Interscience Piiblishers Inc , weighing 36.5 g., m. p. 185-186", was recrystallized from N e w York, N. Y.,1948, p 52 450 ml. of ethanol; yield 28.5 g., 7070, m. p. 190-190.5", ( 3 ) V C G T r e w , T Y Q ~I'uiitif P I V SUC, 37, $76 (1911) raiser1 to 191-191.5" by two further recrystallizations from ct hanol. 1)EPT. OF CHEMISTRY ~JNIVRRSITY OF S O U r l I & K N c.l d $ i i t ~ I . Calcd. for C11H1304S: C, 59.19; H, .5.87. ~ < E C E I V E l >hI %> :: 1, 1 ! ~ ~ 0I'ounti: C, 59.23; Ii, 6.89. L o b ANGP:LE~7 , CALIIS, Ethyl p-i o-To1oxy)-lactate.-Nine grams of O - ( o Loloxy) -1.ictic acidS was converted to the ester by refluxing
