Acetone → p-Toluenesulfonic acid

HRID 2351537Notes

Reaction equation

HRID 2351537 reaction equation
CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(O)=O.O.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22]([OH:25])(=[O:24])=[O:23])=[CH:18][CH:17]=1.C(OO)(=O)C.CC(C)=O>O>[C:16]1([CH3:26])[CH:17]=[CH:18][C:19]([S:22]([OH:25])(=[O:23])=[O:24])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 6585Peracetic AcidHCID 110826-Aminopenicillanic acidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 6101p-Toluenesulfonic acidYield 162.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
7.5 °C

Procedure

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.

Workup

  1. customwas continued at 0° C. until a homogeneous solution
  2. customwas formed
  3. stirringAfter completion of the dropping, the liquid was stirred for 1 hour on an ice bath
  4. filtrationThe precipitated crystal was recovered by filtration
  5. washwashed with diethyl ether
  6. customdried under a reduced pressure

Sources & evidence

ORD record
ord-1fe0ff0ba39a4179832b2f936f135b6c
Source dataset
uspto-grants-1989_10
Patent number
US04873301

Reaction notes

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