Dibutyl 4-benzyloxybenzylphosphonate → Dibutyl 4-hydroxybenzylphosphonate

HRID 1488342Notes

Reaction equation

HRID 1488342 reaction equation
C([O:8][C:9]1[CH:27]=[CH:26][C:12]([CH2:13][P:14](=[O:25])([O:20][CH2:21][CH2:22][CH2:23][CH3:24])[O:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][P:14](=[O:25])([O:15][CH2:16][CH2:17][CH2:18][CH3:19])[O:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 22904634Dibutyl 4-benzyloxybenzylphosphonateHCID 178418361HCID 178418361, compound

Product 1

HCID 22904633Dibutyl 4-hydroxybenzylphosphonate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of dibutyl 4-benzyloxybenzylphosphonate (4.07 g) in ethyl acetate (60 ml) is added 10% palladium on carbon (0.41 g) and the mixture shaken under 25 psi of hydrogen for about 20 hours. The mixture is filtered, concentrated in vacuo, and the residue purified by HPLC, eluting with a gradient of 50-65% ethyl acetate in hexane, to give dibutyl 4-hydroxybenzylphosphonate.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated in vacuo
  3. customthe residue purified by HPLC
  4. washeluting with a gradient of 50-65% ethyl acetate in hexane

Sources & evidence

ORD record
ord-c05ff1b3ffd0424c800bd42612b21eba
Source dataset
uspto-grants-1997_10
Patent number
US05674482

Reaction notes

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