Hydrogen Peroxide → Bis(2-phenylethyl)phosphinic acid

HRID 1683659Notes

Reaction equation

HRID 1683659 reaction equation
[OH:1]O.[C:3]1([CH2:9][CH2:10][P:11]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[OH:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO>[C:3]1([CH2:9][CH2:10][P:11]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:1])[OH:12])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 16220458HCID 16220458, compound

Product 1

HCID 15121925Bis(2-phenylethyl)phosphinic acidYield 30.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrogen peroxide (0.45 mL, 30%, 4.36 mmol) was added dropwise over 1 minute to crude bis(2-phenylethyl)phosphinous acid (1.12 g, 4.34 mmol) in methanol (6.5 mL). After 16 hours, the solvent was evaporated. The residue was basified with 1M NaOH and extracted twice with hexanes. The aqueous layer was acidified with 12M HCl, and the precipitate was filtered, rinsed with water, and dried in vacuo, affording crude product (628 mg) mp 70°-77° C., which was recrystallized from hot ethanol-water (50:50) to give bis(2-phenylethyl)phosphinic acid (364 mg) as a white solid, mp 84°-87° C. NMR δ2.02 (4H, m), 2.94 (4H, q), 6.8 (1H, br. s), 7.24 (10H, m).

Workup

  1. customthe solvent was evaporated
  2. extractionextracted twice with hexanes
  3. filtrationthe precipitate was filtered
  4. washrinsed with water
  5. customdried in vacuo
  6. customaffording crude product (628 mg) mp 70°-77° C., which
  7. customwas recrystallized from hot ethanol-water (50:50)

Sources & evidence

ORD record
ord-8afc4010d40f463889a3bebf9ecbdd36
Source dataset
uspto-grants-1997_06
Patent number
US05639732

Reaction notes

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