Acetic Acid → p-Toluenesulfonic acid

HRID 1706194

Reaction equation

HRID 1706194 reaction equation
COC1C=CC(C[O:8][N:9]([CH2:20][CH2:21][CH2:22][P:23](=[O:30])([O:27]CC)[O:24]CC)[S:10]([C:13]2[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=CC=1.Cl.C(O)(=[O:36])C>>[C:16]1([CH3:17])[CH:15]=[CH:14][C:13]([S:10]([OH:11])(=[O:12])=[O:36])=[CH:19][CH:18]=1.[OH:8][NH:9][CH2:20][CH2:21][CH2:22][P:23](=[O:24])([OH:30])[OH:27]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 20337206diethyl 3-[N-(p-methoxybenzyloxy)-N-tosylamino]propylphosphonate

Product 2

HCID 6101p-Toluenesulfonic acidHCID 3421703-(Hydroxyamino)propylphosphonic acid

Procedure

A mixture of diethyl 3-[N-(p-methoxybenzyloxy)-N-tosylamino]propylphosphonate (3.0 g), 6 N hydrochloric acid (25 ml) and acetic acid (25 ml) was refluxed with stirring for 12 hours. The resultant mixture was concentrated under reduced pressure to give a brownish oily residue. The residue was washed with ethyl ether (100 ml), and then water (100 ml) was added thereto with stirring. Insoluble materials were filtered off from the mixture, whereafter the filtrate was washed with ethyl ether, and then treated with an activated charcoal. The aqueous solution was concentrated under reduced pressure to give a faint yellowish oily residue. The residue was allowed to stand overnight in desiccator under reduced pressure to give crystals. The crystals were washed with ethyl ether to give p-toluene sulfonic acid salt of 3-(N-hydroxyamino)propylphosphonic acid (1.50 g) in the form of fiant yellowish crystals. MP: 129°-135° C.

Workup

  1. temperaturewas refluxed
  2. concentrationThe resultant mixture was concentrated under reduced pressure
  3. customto give a brownish oily residue
  4. washThe residue was washed with ethyl ether (100 ml)
  5. additionwater (100 ml) was added
  6. stirringwith stirring
  7. filtrationInsoluble materials were filtered off from the mixture, whereafter the filtrate
  8. washwas washed with ethyl ether
  9. additiontreated with an activated charcoal
  10. concentrationThe aqueous solution was concentrated under reduced pressure
  11. customto give a faint yellowish oily residue
  12. waitto stand overnight in desiccator under reduced pressure
  13. customto give crystals
  14. washThe crystals were washed with ethyl ether

Sources & evidence

ORD record
ord-88ecc5103d5e4bed93e8ad4462863192
Source dataset
uspto-grants-1980_06
Patent number
US04206156

Linked notes

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