p-Chlorobenzenesulfonic acid → Tris(3-methylbutyl)phosphine oxide

HRID 1252785Notes

Reaction equation

HRID 1252785 reaction equation
[CH2:1]([P:6](=S)([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH2:2][CH:3]([CH3:5])[CH3:4].ClC1C=CC(S(O)(=O)=[O:26])=CC=1>ClC1C=CC=CC=1>[CH2:1]([P:6](=[O:26])([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 7400p-Chlorobenzenesulfonic acidHCID 53965675HCID 53965675, compound

Product 1

HCID 134820Tris(3-methylbutyl)phosphine oxide

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

4.1 g (15 mmol) of triisoamylphosphine sulfide in 70 ml of chlorobenzene (b.p.=132° C.) are combined with 34.7 g (0.18 mol) of p-chlorobenzenesulfonic acid and then heated for 8 hours at reflux. After cooling to room temperature, the reaction mixture is extracted several times with 80 ml portions of ice water and then the chlorobenzene solution is washed with sodium bicarbonate solution. The solution is dried over sodium sulfate and the chlorobenzene is removed in vacuum. Yield: 3 g of solid identified by mass spectroscopy as triisoamylphosphine oxide.

Workup

  1. temperatureheated for 8 hours
  2. temperatureat reflux
  3. extractionthe reaction mixture is extracted several times with 80 ml portions of ice water
  4. washthe chlorobenzene solution is washed with sodium bicarbonate solution
  5. dry with materialThe solution is dried over sodium sulfate
  6. customthe chlorobenzene is removed in vacuum

Sources & evidence

ORD record
ord-7669e54d76d145c39958610ec04de177
Source dataset
uspto-grants-1988_05
Patent number
US04745224

Reaction notes

Loading…