1-Octene → HCID 13751189, compound

HRID 1476012Notes

Reaction equation

HRID 1476012 reaction equation
[PH2:1](=[O:3])[OH:2].[CH2:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]>O1CCCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>[CH2:4]([P:1]([OH:2])[OH:3])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 2

HCID 81251-OcteneHCID 4124402Phosphinic Acid

Product 1

HCID 13751189HCID 13751189, compoundYield 87.5%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

99 g (0.75 mol) of phosphinic acid, 86 g (0.76 mol) of octene, 34 mg of tris(dibenzylideneacetone)dipalladium and 48 mg of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene in 750 g of tetrahydrofuran are reacted at about 70° C. for 9 hours, passed through a column charged with Deloxan® THP II for purification and freed of solvent in a rotary evaporator. The residue is admixed with 500 g of completely ion-free water and stirred, and then filtered, the filtrate is extracted with ethyl acetate. This is followed by removal of solvent in a rotary evaporator to obtain 117 g (84% of theory) of octylphosphonous acid.

Workup

  1. customfreed of solvent in a rotary evaporator
  2. filtrationfiltered
  3. extractionthe filtrate is extracted with ethyl acetate
  4. customThis is followed by removal of solvent in a rotary evaporator

Sources & evidence

ORD record
ord-f0147511f09645918dc7aa6c2d219f22
Source dataset
uspto-grants-2015_04
Patent number
US09018413B2

Reaction notes

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