Oxidation with lead tetra-acetate. n-Butyl glyoxylate

OXIDATION WITH LEAD TETRA-ACETATE n-BUTYL GLYOXYLATE 

An interesting application of lead tetra acetate is to the jireparation of the otherwise dilliculty-accessiblo a-butyl glyoxylate (II) by oxidation of di-a-butyl i-tartrate (I)  

Place a mixture of 125 ml. of A.R. benzene and 32 -5 g. of di-re-butyl d-tartrate (1) in a 500 ml. three-uccked flask, equipped with a Hershberg stirrer (Section 11,7) and a thermometer. Stir the mixture rapidly and add 58 g. of lead tetra-acetate (Section 11,50,15) in small portions over a period of 20 minutes whilst maintaining the temperature below 30° by occasional cooling with cold water. Continue the stirring for a further 60 minutes. Separate the salts by suction filtration and wash with two 

portions of benzene. Remove the benzene and acetic acid from the filtrate by flash distillation (compare Section 11,13) and distil the residue under diminished pressure, preferably in a slow stream of nitrogen. Collect the n-butyl glyoxylate (2) at 66-69°/5 mm. The yield is 26 g. 

Methyl ethyl ketone is allowed to react with n-butyl or iso-amyl nitrite in the presence of hydrochloric acid to yield diacetyl monoxime (nitrosomethyl ethyl ketone)  

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VI.37. OXIDATION WITH LEAD TETRA-ACETATE n-BUTYL GLYOXYLATE... 

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