Acetone → p-Toluenesulfonic acid

Participants

Reaction Conditions

Reaction Steps

6-Aminopenicillanic acid (43.2 g, 200 millimoles) was dispersed in distilled water at 0° C., and p-toluene-sulfonic acid monohydrate (38.0 g, 200 millimoles) was added to the dispersion with stirring, which was continued at 0° C. until a homogeneous solution was formed. Then, a 40% aqueous solution of peracetic acid (40.0 g, 210 millimoles) was gradually dropped into the solution so that the temperature of the reaction liquid was maintained at 5 to 10° C. After completion of the dropping, the liquid was stirred for 1 hour on an ice bath, and 150 ml of acetone was added to the liquid. The precipitated crystal was recovered by filtration, washed with diethyl ether and dried under a reduced pressure to obtain 56.0 g (69.2%) of a p-toluenesulfonic acid salt of 6-aminopenicillanic acid sulfoxide.

Provenance & Evidence