Toluene → n-Butanephosphonic acid n-butyl-(3-nitrophenyl) ester

HRID 1287313Notes

Reaction equation

HRID 1287313 reaction equation
[Cl-].[CH2:2]([O:6][P:7]([CH2:10][CH2:11][CH2:12][CH3:13])(=[O:9])[OH:8])[CH2:3][CH2:4][CH3:5].[N+:14]([C:17]1C=C([O-])[CH:20]=[CH:21][CH:22]=1)([O-:16])=[O:15].[Na+].[C:25]1(C)C=CC=C[CH:26]=1>>[CH2:4]([C:3]1[C:17]([N+:14]([O-:16])=[O:15])=[CH:22][CH:21]=[CH:20][C:2]=1[O:6][P:7]([CH2:10][CH2:11][CH2:12][CH3:13])(=[O:8])[OH:9])[CH2:5][CH2:25][CH3:26]

Participants

4

Reactant 3

HCID 1140TolueneHCID 86734044n-Butanephosphonic acid n-butyl ester chlorideHCID 101286967CID 101286967

Product 1

HCID 54481294n-Butanephosphonic acid n-butyl-(3-nitrophenyl) ester

Procedure

20 g of n-butanephosphonic acid n-butyl ester chloride are added dropwise to a suspension of 14.3 g of sodium 3-nitrophenolate in 170 ml of toluene at 20° C. After 4 hours, the mixture is filtered, the filtrate is evaporated and the residue is distilled in vacuo at 0.1 mm Hg. 16 g of n-butanephosphonic acid n-butyl-(3-nitro-phenyl) ester are obtained. After reduction with hydrogen and palladium on charcoal, in isopropanol, at 1 atmosphere pressure, 13.8 g of n-butanephosphonic acid n-butyl-(3-aminophenyl) ester are obtained.

Workup

  1. filtrationthe mixture is filtered
  2. customthe filtrate is evaporated
  3. distillationthe residue is distilled in vacuo at 0.1 mm Hg

Sources & evidence

ORD record
ord-b27ad6561a674dbda93a5ed7932fb409
Source dataset
uspto-grants-1976_10
Patent number
US03984432

Reaction notes

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