Cl[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH:9]=O)[C:7]=1[CH3:8].[ClH:11].[C:12]([CH2:15][O:16][NH2:17])([OH:14])=[O:13].C(CON)(O)=O.C([O-])(=O)C.[Na+].[OH-].[Na+]>O.C(O)C>[Cl:11][CH:15]([O:16][N:17]=[CH:9][C:6]1[C:7]([CH3:8])=[CH:2][CH:3]=[CH:4][CH:5]=1)[C:12]([OH:14])=[O:13]A warm solution of 1.5 gm. (0.01 mole) of 6-chloro-o-tolualdehyde in 15 ml. of ethanol was stirred into a solution of 1.1 gm. (0.010 equiv.) of carboxymethoxylamine hemihydrochloride and 1.3 gm. (0.016 equivs.) of anhyd. sodium acetate in 15 ml. water. After heating a half hour on the steam bath, the reaction mixture was cooled and adjusted to pH 8 with 5% aqueous sodium hydroxide. The mixture was extracted with ether, and the ether extract was discarded. The alkaline-aqueous phase was then adjusted to pH 5 with hydrochloric acid and was evaporated to 25 ml. volume. It was then acidified to pH 1.5-2.0 with cooling in ice bath. The solid was removed by filtration, was washed with cold water, and was dried in air to obtain 1.5 gm. (68%) of crude product melting at 121°-6° C. Recrystallization from aqueous-ethanol yielded 1.4 gm. of product melting at 124°-7° C. (dried at 65° C. in vacuo).
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