Acetic Acid → p-Toluenesulfonic acid

HRID 2051983

Reaction equation

HRID 2051983 reaction equation
COC1C=CC(C[O:8][N:9]([CH2:20][CH2:21][CH2:22][P:23](=[O:34])([O:29]CCCC)[O:24]CCCC)[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:40])C.C>O>[C:16]1([CH3:17])[CH:15]=[CH:14][C:13]([S:10]([OH:11])(=[O:12])=[O:40])=[CH:19][CH:18]=1.[OH:8][NH:9][CH2:20][CH2:21][CH2:22][P:23](=[O:24])([OH:34])[OH:29]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 297MethaneHCID 313Hydrochloric AcidHCID 20185706dibutyl 3-[N-(p-methoxybenzyloxy)-N-tosylamino]propylphosphonate

Product 2

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of dibutyl 3-[N-(p-methoxybenzyloxy)-N- tosylamino]propylphosphonate (28.4 g), 6N hydrochloric acid (280 ml) and acetic acid (280 ml) was refluxed with stirring for 20 hours. The resultant mixture was concentrated under reduced pressure to give a residue, and then water was added thereto. The mixture was treated with an activated charcoal, whereafter the mixture was concentrated under reduced pressure to give an oily residue. The oily residue was washed with ether and dried under reduced pressure. The solid was washed with acetonitrile and ethyl ether to give p-toluenesulfonic acid salt of 3-(N-hydroxyamino)propylphosphonic acid (12.4 g) in the form of crystals. MP: 129°~135° C.

Workup

  1. temperaturewas refluxed
  2. concentrationThe resultant mixture was concentrated under reduced pressure
  3. customto give a residue
  4. concentrationwas concentrated under reduced pressure
  5. customto give an oily residue
  6. washThe oily residue was washed with ether
  7. customdried under reduced pressure
  8. washThe solid was washed with acetonitrile and ethyl ether

Sources & evidence

ORD record
ord-7332eab08f234102b5dfa87ee9ac43f0
Source dataset
uspto-grants-1980_01
Patent number
US04182758

Linked notes

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