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INDUSTRIAL AND ENGINEERING CHEMISTRY
to 0" C. and neutralized irith hydrochloric acid. In the presence of phenylacetic acid and sodium chloride, large amounts of phenylmalonic acid are carried down. The phenylacetic acid may be removed by extraction with benzeue. Phenylmalonic acid can be separated iroin the Tater and salt by extraction rvith ethyl ether. Evaporation of the ether under vacuum gives fairly pure phenylmalonic acid (melting point, 145" to 148' C.). Since phenylmalonic acid readily decarboxylates to phenylacetic acid, care must be taken in both neutralization and evaporat,ion steps to avoid temperatures above 30 C. ACKNOWLEDGMENT
The authors TTish to express their thanks to V. L. Hamley for his suggestions arid assistance during the course of this xork. LITERATURE CITED
(I) Bockmuhl,AI.. and Erhart. G . , U. S. P a t e n t 2,012,372 (1935). ( 2 ) Bigre-Smith, ll,, m d T u ~ n e i F., . J . Cheni. SOC.,1950, 1975.
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(3) Franipton, O., and Yohis, J . F., IVD. EKG.C x m . , 45, 4114 (1953). (4) Gilman, H., a n d Pacevitz, H. A , , J . Am. Chem. SOC.,62, l:Wl (1940). ( 6 ) Gilman, H., Pacevitz, H. A , aiicl Baine, O., Ibid., 62, 1514 (1940). (6) Hansley. v. L., I S D . E N G . CHE;..?I., 39, 5 5 (1947). ( 7 ) Ibid., 43, 1769 (1951). (8) Letsinger. R. L., ,I. Am. Chem. Soc.. 70, 406 (1948). (9) Morton, A. A, Fall.iYel1, F., and Palmer, L., Ibid., 60, 1421i (1938). (10) I l o r t o n , A. d.,and IIeckenbleikner, I., [hid.,58, 2699 (19%). (I 1) I l o r t o n , -4.A , , and liedniaii, L. 31., ISD. ENG.
