Sodium Hydroxide → HCID 54412899, compound

HRID 1586759Notes

Reaction equation

HRID 1586759 reaction equation
[N+:1]([C:4]1[C:13]([CH2:14][P:15]([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])=[O:16])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8]C)=[O:7])([O-:3])=[O:2].[OH-].[Na+]>C(O)C>[N+:1]([C:4]1[C:13]([CH2:14][P:15]([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])=[O:16])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54332340HCID 54332340, compound

Product 1

HCID 54412899HCID 54412899, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 2-nitro-3-(diethylphosphonomethyl)benzoate (7.3 gm) was dissolved in absolute ethanol (44 mL) containing sodium hydroxide (0.89 gm) and allowed to stir at room temperature for 48 hours. The solvent was removed on a rotory evaporator and the residue dissolved in water (150 mL) and extracted with ethyl acetate (100 mL). The aqueous layer was acidified with 1N HCl and the turbid solution extracted with 3×chloroform (75 mL). The chloroform layers were combined, dried (MgSO4) and concentrated to a yellow solid. 1H NMR data CDCl3, TMS 1.28 (t, 6H), 3.27 (d, 2H), 4.09 (p, 4H), 7.57 (t, 1H), 7.83 (d, 1H), 7.98 (d, 1H).

Workup

  1. customThe solvent was removed on a rotory evaporator
  2. dissolutionthe residue dissolved in water (150 mL)
  3. extractionextracted with ethyl acetate (100 mL)
  4. extractionthe turbid solution extracted with 3×chloroform (75 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to a yellow solid

Sources & evidence

ORD record
ord-7e88e825417d43dba4c4728502710116
Source dataset
uspto-grants-1993_06
Patent number
US05216003

Reaction notes

Loading…