814COHEN, DUGHI, NOTARO, AND PINKUS VOL. 27 sodium hydroxide solution essentially as described above for IVa. After stirring for 36 hr., the mixture was worked up to give 0.52 g. (33%) of phthalic acid, m.p. 187-188O and at 192-193' (sealed tube) after one recrystallization from water. Lit.88m.p. 191' (sealed tube) (identified as described above).Independent synthesis of XXII was accomplished by refluxing a solution of 41.6 g. (0.225 mole) of o-xylyl bromide and 23.7 g. (0.225 mole) of 2,2'-iminodiethanol in 400 ml. of acetonitrile for 1.5 days. The acetonitrile wa, q distilled, and a cold solution of 13.0 g. of sodium hydroxide in 100 ml. of water was added. The resulting basic mixture was extracted (33) See ref. 22, p. 192. three times with ether and the ether extracts dried over anhydrous magnesium sulfate. The solvent was removed, and the residue was distilled t o give 34.0 g. (72%) of amino dialcohol XXII, b.p. 153-155' at 0.55 mm. and at 172-174" at 0.95-1.00 mm. on redistillation.
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