July, 1925GGRMANIUM ARYL AND ALKYL COMPOUNDS 2039 6 or more moles of sodium hydroxylamine disulfonate which rapidly hydrolyzed to an acid solution of monosulfonate.Preparation of Dimethylg1yoxime.-The biacetyl monoxime and monosulfonate were filtered to remove any sediment, mixed in a 15-liter flask, the mixture was heated to 70" and allowed to remain warm and occasionally stirred for several hours. The dimethylglyoxime separated in crystals that were filtered from the solution after it had become cold. They were washed with cold water until free from sulfate; yield, 575 g. ; 235-240'.Recrystallization was unnecessary since the product was pure white and free from tarry matter. SummaryA study has been made of the conditions affecting the formation of dimethylglyoxime, and simplified and efficient methods have been devised for the preparation of biacetyl monoxime, sodium hydroxylamine monosulfonate and dimethylglyoxime.

Table IICatalytic Reduction of Some Typical Unsaturated 1,4-Diketones and Related Compounds Except as otherwise indicated these reductions were carried out at 25-27°and atmospheric pressure, using the platinum oxide catalyst (0.01-0.02 g. per g. of substance) in 95% ethanol as solvent (35-70 cc. per gram of substance). Yield of mono-Compound molecular product, % Cw-dibenzoylethylene 45-50°T raMS-dibenzoylmethylethylene 75 Cw-dibenzoylphenylethylene 62 (25b) T>a«s-di(2,4,6-trimethylbenzoyl)ethylene86 7>ans-di( 4-chlorobenzoyl) ethylene 44 T ra«i-di(4-methylbenzoyl)ethylene 19 Dibenzoylmethoxyethylene C C'«-dibenzoylbromoethylene!Í 40 Cii-dibenzoyldibromoethylene'* 84 Dibenzoylbromoethaned 68 dZ-Dibenzoyldibromoethane11 44 0The rest of the material was accounted for as oils and small amounts of dimolecular products totaling 10-20%

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The oxidation of salicylic acid to gentisic acid by persulfate ion has been described (1, 2, 3). Recently a more complete study of the products of the reaction has revealed in addition to gentisic acid the presence of 2,3-dihydroxybenzoic acid to the extent of 15% of the total product (4). This is apparently the first published report of ortho attack even though the para position was unsubstituted. Prior to this communication ortho substitution was reported only when the para position was blocked (5).