Dibenzyl 3,4,5-trimethoxyphenylphosphonate → 3,4,5-Trimethoxyphenylphosphonic Acid

HRID 48082

Reaction equation

HRID 48082 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([P:13](=[O:30])([O:22]CC2C=CC=CC=2)[O:14]CC2C=CC=CC=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]>C(OCC)(=O)C.[Pd]>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([P:13](=[O:14])([OH:30])[OH:22])[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

4

Reactant 1

HCID 54545930Dibenzyl 3,4,5-trimethoxyphenylphosphonate

Product 1

HCID 206320103,4,5-Trimethoxyphenylphosphonic Acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of dibenzyl 3,4,5-trimethoxyphenylphosphonate 2 (1 mmol) in 30 mL of ethyl acetate is added 10% Pd on carbon (0.10 g). The mixture is stirred under an atmosphere of hydrogen for 16 hours. Mixture is filtered through celite and washed with methanol (3×10 mL). All washings and filtrate are combined and concentrated to give 3,4,5-trimethoxyphenylphosphonic acid 3.

Workup

  1. filtrationMixture is filtered through celite
  2. washwashed with methanol (3×10 mL)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2dcfab923fbe41a4835acae0771e351a
Source dataset
uspto-grants-2004_03
Patent number
US06702705B1

Linked notes

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