Diphenyl Ether → Di-n-octylphosphinic acid

HRID 625205

Reaction equation

HRID 625205 reaction equation
C1([Bi](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1([O:26]C2C=CC=CC=2)C=CC=CC=1.C(O)(=O)CCCCCCC/C=C\CCCCCCCC.C(N)CCCCCCC/C=C\CCCCCCCC.[Se].C(P(CCCCCCCC)CCCCCCCC)CCCCCCC.C([P:106](=[O:123])([CH2:115][CH2:116][CH2:117][CH2:118][CH2:119][CH2:120][CH2:121][CH3:122])[CH2:107][CH2:108][CH2:109][CH2:110][CH2:111][CH2:112][CH2:113][CH3:114])CCCCCCC>C=CCCCCCCCCCCCCCCCC.C1(C)C=CC=CC=1.CO.C(#N)C.CN1CCCC1=O>[CH2:115]([P:106]([CH2:107][CH2:108][CH2:109][CH2:110][CH2:111][CH2:112][CH2:113][CH3:114])(=[O:123])[OH:26])[CH2:116][CH2:117][CH2:118][CH2:119][CH2:120][CH2:121][CH3:122]

Participants

13

Reactant 7

HCID 7583Diphenyl EtherHCID 11774Triphenylbismuth2×HCID 20851TrioctylphosphineHCID 65577Trioctylphosphine oxideHCID 445639Oleic AcidHCID 5356789OleylamineHCID 6326970Selenium2×

Product 1

HCID 99411Di-n-octylphosphinic acid

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 6342AcetonitrileSolventHCID 82171-OctadeceneSolvent3×HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Materials. 1-methyl-2-pyrrolidinone (99.5%, Aldrich), 1-octadecene (90%, Aldrich), acetonitrile (99.9%, Fisher Chemical), triphenylbismuth (99%, Strem), CdO (99.5%, Aldrich), diphenyl ether (99%, Aldrich), methanol (ACS grade, VWR), oleic acid (90%, Aldrich), oleylamine (70% Aldrich), selenium (99.99%, Strem), trioctylphosphine (90%, Aldrich), trioctylphosphine oxide (99%, Strem), toluene (ACS grade, VWR). 0.2M Se-ODE was prepared by dissolving selenium powder in 1-octadecene at 200° C. for 2 hr under inert atmosphere according to the procedure by Bullen et al.[42]; trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile prior to use; di-n-octylphosphinic acid (DOPA) was synthesized according to the procedure reported by Wang et al.[1]; a stock suspension of 2 mM triphenylbismuth (BiPh3) in 1-octadecene was prepared in advance.

Workup

  1. custom0.2M Se-ODE was prepared
  2. customtrioctylphosphine oxide (TOPO) was recrystallized from acetonitrile
  3. customwas prepared in advance

Sources & evidence

ORD record
ord-9c3a268df10549b2be3b6aeb3d49fbb1
Source dataset
uspto-grants-2016_04
Patent number
US09306110B2

Linked notes

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