Diethyl benzylphosphonate → Phosphonic acid, benzyl-, monoethyl ester

HRID 325249Notes

Reaction equation

HRID 325249 reaction equation
[CH2:1]([P:8](=[O:15])([O:12]CC)[O:9][CH2:10][CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CCO>[CH2:10]([O:9][P:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:12])[OH:15])[CH3:11]

Participants

4

Reactant 2

HCID 14122Diethyl benzylphosphonateHCID 14798Sodium Hydroxide

Product 1

HCID 177024Phosphonic acid, benzyl-, monoethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl benzylphosphonate (5.0 mL, 5.5 g, 24 mmol) was dissolved in absolute EtOH (25 mL), then 50% NaOH (3 mL) was added. The reaction was heated under reflux overnight, allowed to cool to RT, then partitioned between 2N HCl and EtOAc. Washed organic layer with brine, extracted combined aqueous layers with EtOAc, dried combined organic layers over Na2SO4. After filtration and concentration recovered 4.5 g (93%). MS (DCI/NH3) 201/218 (M+H)+/(M+H+NH3)+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux overnight
  3. custompartitioned between 2N HCl and EtOAc
  4. extractionWashed organic layer with brine, extracted
  5. customdried
  6. filtrationAfter filtration and concentration
  7. customrecovered 4.5 g (93%)

Sources & evidence

ORD record
ord-86af75f8b06e47cfba75eb14bb2d8d33
Source dataset
uspto-grants-2001_04
Patent number
US06221865B1

Reaction notes

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