Sulfuric Acid → HCID 178527055, Verbindung

HRID 490925

Reaktionsgleichung

Reaktionsgleichung von HRID 490925
O.[PH2:2]([O-:4])=[O:3].[Na+].[C:6]1([CH2:12][CH2:13][CH:14]=[CH2:15])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.N(C(C)(C)C#N)=NC(C)(C)C#N.S(=O)(=O)(O)O.C12(N)CC3CC(CC(C3)C1)C2>C(O)C>[C:6]1([CH2:12][CH2:13][CH2:14][CH2:15][PH:2](=[O:4])[OH:3])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

7

Edukt 5

HCID 1118Sulfuric AcidHCID 2130AmantadineHCID 6547AzobisisobutyronitrileHCID 130333-ButenylbenzeneHCID 178418950HCID 178418950, Verbindung

Produkt 1

HCID 178527055HCID 178527055, VerbindungAusbeute 54,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of sodium hypophosphite hydrate (17.6 g, 200 mmol), 4-phenyl-1-butene (10 mL, 66.6 mmol), 2,2′-azobisisobutyronitrile (AlBN) (1 g), conc. sulfuric acid (1 mL) in 200 mL of absolute ethanol was heated to reflux for 17 hours. The reaction mixture was concentrated to an oil, suspended in 70 mL of water, made basic with 50% NaOH and washed with 2×70 mL ether. The aqueous layer was acidified with conc. sulfuric acid, extracted into ethyl acetate and concentrated. The residue was dissolved in ether and adamantaneamine (10 g, 66 mmol) was added. A white precipitate was filtered, partitioned between 10% HCl and ethyl acetate. The organic layer was concentrated to provide 4-phenylbutylphosphinic acid (7.2 g).

Aufarbeitung

  1. temperatureto reflux for 17 hours
  2. concentrationThe reaction mixture was concentrated to an oil
  3. washwashed with 2×70 mL ether
  4. extractionextracted into ethyl acetate
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in ether
  7. filtrationA white precipitate was filtered
  8. custompartitioned between 10% HCl and ethyl acetate
  9. concentrationThe organic layer was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-52c6bf5ce5e24e2cb1f5296bf7625900
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528173B2

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