Sulfuric Acid → HCID 178527055, compound

HRID 1677601Notes

Reaction equation

HRID 1677601 reaction equation
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

Participants

7

Reactant 5

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

Product 1

HCID 178527055HCID 178527055, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of sodium hypophosphite hydrate (17.6 g, 200 mmol), 4-phenyl-1-butene (10 mL, 66.6 mmol), 2,2′-azobisisobutyronitrile (AIBN) (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).

Workup

  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

Sources & evidence

ORD record
ord-3f32e978b3094af4a9203e42c70d8297
Source dataset
uspto-grants-2011_08
Patent number
US08008325B2

Reaction notes

Loading…