Vol. 67 droxide according to the method indicated, but not described by Claisen.4 To 125 g. of potassium hydroxide in 400 cc. of absolute alcohol was added 198 g. of a-bromo-/Sethoxypropionaldehydediethylacetal and the mixture refluxed in an atmosphere of nitrogen for two hours. Insoluble solids were filtered off and the filtrate distilled under vacuum.The residue from the distillation was extracted with ether and the extract concentrated and combined with the first distillate. Redistillation yielded 110 g. (80%) of the desired product, b. p. 94-96°( 20 mm.

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filter. It was taken up in 2000 ml. of water at 80°with 5 g. of magnesium oxide and 5 g. of Darco G-60, filtered hot, and the filtrate was then neutralized to pH 4 and cooled to 5°. The bright yellow product was filtered, washed with water and acetone and dried at 50°. The purity, as estimated from the ultraviolet absorption curve, was about 80%. In 0.1 N sodium hydroxide solution it showed maxima at 305 and 378 µ, a plateau at 278-285 µ, and a minimum at 252 µ. In 0.1 N hydrochloric acid it showed a maximum at 307 µ, a plateau at 248-255 µ, and a shoulder at 340-355 µ.Synthesis of Pteroylglutamic Acid by Anaerobic Hydrolysis of 4-Alkylamino Derivatives.-A. From 4-Dimethylaminopteroylglutamic Acid (III).-To 20 ml. of oxygen-free 1 N sodium hydroxide was added 0.200 g. of 69.6% 4-dimethylaminopteroylglutamic acid. The solution was heated on the steam-bath for five hours under nitrogen. It was then diluted to 100 ml., and poured into 45 ml. of 30% acetic acid solution. The mixture was cooled and the precipitate collected; dry weight, 0.0977 g. This material had a chemical assay of 69.9%, and a bioassay of 75% as compared to pteroylglutamic acid as a growth-stimulant for S. faecalis R.B. From 4-(1-Piperidyl)-pteroylglutamic Acid (IV).-A 0.680-g. sample of 4-(1 -piperidyl)-pteroylglutamic acid of 73.4% purity was treated in the same fashion as described above, yielding 0.398 g. of a product with a chemical assay of 63.5%, and a bioassay of 56.5% as growthstimulant for 5. faecalis R.Acknowledgments.-We are indebted to Miss Ruth Abbott for the ultraviolet absorption data, to Mr. O. Sundberg and associates for the microanalyses, and to Mr. Raul Maldonado for the chemical assays.

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