Benzene → 1,2-Bis(o-anisylphenylphosphino) ethane

HRID 27046

Reaction equation

HRID 27046 reaction equation
[CH2:1]([P:10]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([CH2:12][CH2:13][P:14]([CH2:22][C:23]1[C:24]([O:29][CH3:30])=[CH:25][CH:26]=[CH:27][CH:28]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=O)=O)[C:2]1[C:3]([O:8][CH3:9])=[CH:4][CH:5]=[CH:6][CH:7]=1.Cl[SiH](Cl)Cl.C(N(CC)CC)C.C1C=CC=CC=1>CO.C(#N)C>[CH2:1]([P:10]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:12][CH2:13][P:14]([CH2:22][C:23]1[C:24]([O:29][CH3:30])=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:2]1[C:3]([O:8][CH3:9])=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 8471TriethylamineHCID 24811TrichlorosilaneHCID 867345011,2-Bis(o-anisylphenylphosphinyl) ethane2×

Product 1

HCID 150615581,2-Bis(o-anisylphenylphosphino) ethane

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

Reduction of 1,2-bis(o-anisylphenylphosphinyl) ethane was accomplished by refluxing 16.5 g. (0.12 mole) trichlorosilane and 12.2 g. (0.12 mole) triethylamine in 188 ml. of dry benzene for one hour. Then 3.0 g. (0.012 mole) of 1,2-bis(o-anisylphenylphosphinyl) ethane in 75 ml. of dry acetonitrile was added and the mixture refluxed 1.5 hours. Quenching in 30% sodium hydroxide solution followed by separating and evaporating the organic layer gave 1.4 g. of crude crystals which were insoluble in cold methanol. Further crystallization from hot methanol gave 1,2-bis(o-anisylphenylphosphino) ethane, m.p. 102°-104° C., [α]D20 -83.4° (C=0.5 in CHCl3). The mass spectra gave a very strong parent peak at 458 and the nmr confirmed the structure.

Workup

  1. temperatureby refluxing 16.5 g
  2. temperaturethe mixture refluxed 1.5 hours
  3. customQuenching in 30% sodium hydroxide solution
  4. customby separating
  5. customevaporating the organic layer
  6. customgave 1.4 g
  7. customFurther crystallization from hot methanol

Sources & evidence

ORD record
ord-393e2fa1622e4648889c7113444d8e50
Source dataset
uspto-grants-1980_09
Patent number
US04220590

Linked notes

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