Hydrochloric Acid → Phosphonic acid, (p-acetamidophenyl)-

HRID 1451058Notes

Reaction equation

HRID 1451058 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([P:8](=[O:11])([OH:10])[OH:9])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[C:17](OC(=O)C)(=[O:19])[CH3:18].Cl>O>[C:17]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([P:8](=[O:10])([OH:9])[OH:11])=[CH:4][CH:3]=1)(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic Anhydride2×HCID 53590Phosphanilic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 155214Phosphonic acid, (p-acetamidophenyl)-Yield 38.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of (4-aminophenyl)phosphonic acid (Aldrich, 0.00058 mol) in water (1.5 mL) was added sufficient sodium bicarbonate to make a clear solution. To the mixture, acetic anhydride (0.2 mL, 0.002 mol) was added and stirred for 0.5 h. Again, acetic anhydride (0.2 mL, 0.002 mol) was added and stirred for 0.5 h. The mixture was let stand at room temperature for 2 h and then concentrated hydrochloric acid (0.5 mL) was added. Fine white needles separated out which were collected by filtration, washed with water and dried to give 0.048 g (38.5%) of the title compound, mp 228° C. (rep. mp 229° C.--Bauer, H. J. Am. Chem. Soc. 1947, 63, 2137-2138).

Workup

  1. stirringstirred for 0.5 h
  2. customat room temperature
  3. customfor 2 h
  4. customFine white needles separated out which
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-c569f7cd0cf84707af9a61fa029e1fb9
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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