Dec., 194s AMIDES FROM ALKENES AND MONONITRILES 4045 covered glycol. The acid was also obtained in 36% yield by oxidation of 1-methyl-I-cyclopentene following the procedure given above for the diol. 6-Ketoheptanoic Acid.l9-This acid, b. p. 154-158' (2 mm.), (neut. equi-v. 142, calcd. 144) was obtained in 57% yield, or 84y0 if allowance is made for recovered glycol, by the oxidation of l-i~ethyl-1,2-cyclohcxanediol (13 9.) with permanganate in acetone as described for 5-ketohexanoic acid. The acid gave a semicarbazone, ,m. p. 144°,20 a 2,4-dinitrophenylbydrazone, m. p. 82-83 , and a p-nitrophenylhydrazone, m. p . 112'. 4-Methyl-5-ketocaproic Acid.-This acid (neut. equiv. 145, calcd. 144), b. p. 120-130 (1 mm.), was obtained in 43-46y0 yield from 1,2-dimethyl-2,3-cyclopentene and from 1,2-dimethyl-2,3-cyclopentenediol using the permanganate in acetone procedure described above. The acid gave a semicarbazone, m. p. 16&169°.21Oxidation of 1,2 -Dimethyl-1 -cyclopentene.-The application of the permanganate in acetone procedure to 1,2-dimethyl-1-cyclopentene (19.2 g.) gave a small amount of acids (2.4 g.) and neutral products (11.1 g.), b. p. 58-72". The neutral product gave a p-nitrophenylhydrazone, m. p. 158;160", and a 2,4-dinitrophenylhydrazone, m. p. 196-198 .CY -M ethylglutaric: Acid.-1 -Methyl -2,3-cyclopentanediol (11.6 9.) in a mixture of 16 ml. of sulfuric acid and 200 ml. of water, was oxidized at about 0" with chromic acid. Chromic anhydride (20 g.) was added in 1-2 g. portions, allowing time for the decolorization of one portion before the next was added. The reaction mixture was warmed up to 40" after the addition of the last portion of the oxidizing agent and extraxted with a liter of ethyl acetate in five portions. The ethyl acetate was distilled and the residue extracted with a solution containing 8 g. of sodium hydroxide in 60 ml. of water. Theunoxidized glycol (4 g.) was extracted with ethyl acetate. The alkaline solution was made acid with sulfuric acid and the organic acid extracted with ethyl acetate. After distillation of ethyl acetate the acids were distilled a t 150-180' (2 mm.). The distillate crystal-