p-Toluenesulfonic acid monohydrate → p-Toluenesulfonic acid

HRID 259161Notes

Reaction equation

HRID 259161 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1>CC(C)=O>[CH3:12][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 6101p-Toluenesulfonic acidYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred slurry of 6-triphenylmethylamino-2,2-dimethyl-3-(0,0-dimethylphosphono)penam, 487 mg. (0.001 mole), in 10 ml. of dry acetone is added 190 mg. (0.001 mole) of p-toluenesulfonic acid monohydrate at 25° C. The solids dissolve slowly, giving a clear solution. After stirring at 25° C. for 15 minutes the product starts to pecipitate. Stirring is continued for a further 45 minutes after the product starts to appear. The first crop is then filtered off, washed with acetone, and dried to afford the title compound as the p-toluenesulfonate salt. 1H-nmr (DMSO-d6) ppm (δ): 1.65 (s,3,,CH3), 1.70 (s,3,,CH3), 2.32 (s,3,,CH3), 3.77 (d,J = 11,6,,OCH3), 4.11 (d,J = 11, 1,C-3,) 5.1 (m,1)- and 5.45 (d,J = 4,1)-C-5 and C-6 protons, 7.3 (q,4,aromatic protons). The yield is 83% of theory, M.P. 149°-151° C.

Workup

  1. customat 25° C
  2. dissolutionThe solids dissolve slowly
  3. customgiving a clear solution
  4. stirringStirring
  5. waitis continued for a further 45 minutes
  6. filtrationThe first crop is then filtered off
  7. washwashed with acetone
  8. customdried

Sources & evidence

ORD record
ord-bff3c46d82b24ee28d74fccb1a7e97d4
Source dataset
uspto-grants-1977_07
Patent number
US04036846

Reaction notes

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