Diethyl 5-[(diethoxyphosphinyl)methyl]-1,3-benzenedicarboxylate → 5-(Phosphonomethyl)isophthalic acid

HRID 1352808Notes

Reaction equation

HRID 1352808 reaction equation
C([O:3][P:4]([CH2:9][C:10]1[CH:11]=[C:12]([C:21]([O:23]CC)=[O:22])[CH:13]=[C:14]([C:16]([O:18]CC)=[O:17])[CH:15]=1)([O:6]CC)=[O:5])C>Cl>[P:4]([CH2:9][C:10]1[CH:15]=[C:14]([C:16]([OH:18])=[O:17])[CH:13]=[C:12]([C:21]([OH:23])=[O:22])[CH:11]=1)([OH:6])([OH:5])=[O:3]

Participants

3

Reactant 1

HCID 12017543Diethyl 5-[(diethoxyphosphinyl)methyl]-1,3-benzenedicarboxylate

Product 1

HCID 98783565-(Phosphonomethyl)isophthalic acidYield 43.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of diethyl 5-[(diethoxyphosphinyl) methyl]-1,3-benzenedicarboxylate (0.186 g, 0.5 mmol) in 12 N HCl (2.5 mL) was heated at 100° C. for 24 hours. The resulting precipitate was washed with water and dried under vacuum to give 0.057 g of white powder: 1H NMR (D2O) δ 3.11 (d, 2H), 7.93 (s, 2H), 8.19 (s, 1H). TLC: Rf 0.20 (EtOAc/Hexanes 1/1). Elemental analysis calculated for C9H7O7P.H2O: C, 38.86; H, 3.99. Found: C, 38.74; H, 4.08.

Workup

  1. washThe resulting precipitate was washed with water
  2. customdried under vacuum

Sources & evidence

ORD record
ord-c447904efbd2404c9cc3f82089c5d1eb
Source dataset
uspto-grants-2007_05
Patent number
US07220780B2

Reaction notes

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