Acetone → P-Toluenesulfonylhydrazide

Participants

Reaction Steps

Alternatively, 4-diazo-3-methoxy-2,5-cyclohexadien-1-one can be synthesized chemically. First, 2-methoxy-p-benzoquinone is synthesized by the addition of m-methoxyphenol in acetone to an aqueous solution of potassium nitrosodisulfonate and potassium monobasic phosphate. On treatment of 2-methoxy-p-benzoquinone with p-toluenesulfonhydrazide, the antibiotic is produced. Purification of the product from the reaction mixture is accomplished by chromatography on a silica gel column with chloroform:methanol (9:1, v/v).

Provenance & Evidence