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

HRID 23590Notes

Reaction equation

HRID 23590 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 (41% yield).

Workup

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

Sources & evidence

ORD record
ord-d14b9ee7b9394b93acd035e1bfcc1e4b
Source dataset
uspto-grants-2005_02
Patent number
US06852750B2

Reaction notes

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