Hydrochloric Acid → Triphenylphosphine Oxide

HRID 1970092Notes

Reaction equation

HRID 1970092 reaction equation
[C:1]1([P:7](=[O:20])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[Al].Cl>C(#N)C>[C:14]1([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1.[C:1]1([P:7](=[O:20])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 13097Triphenylphosphine OxideHCID 65578Oxalyl chlorideHCID 5359268Aluminum

Product 2

HCID 11776TriphenylphosphineYield 4%HCID 13097Triphenylphosphine OxideYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triphenylphosphine oxide (1.405 g, 5.0 mmol) and acetonitrile (5 mL) were weighted out into a reactor, then oxalyl chloride (0.43 mL, 5.05 mmol) was added thereto under room temperature, and the mixture was stirred for 10 minutes. Then, previously shredded aluminum foil (135 mg, 5.0 mmol) was added to this reaction solution, and subsequently the mixture was stirred for 1 hour under room temperature to cause a reaction. The reaction solution was poured into an iced 5% hydrochloric acid aqueous solution from the reactor, to terminate the reaction, and thereafter the organic layer was separated, and the water layer was extracted with ethyl acetate for 3 times. The organic layers were combined into one, washed with saturated saline, dried on sodium sulfate and concentrated under reduced pressure. The residue was purified with a silica gel column chromatography to give triphenylphosphine (47 mg, 0.18 mmol, yield: 4%) and triphenylphosphine oxide (1.32 g, 4.75 mmol, collection rate: 94%).

Workup

  1. stirringsubsequently the mixture was stirred for 1 hour under room temperature
  2. customa reaction
  3. customto terminate
  4. customthe reaction
  5. customthe organic layer was separated
  6. extractionthe water layer was extracted with ethyl acetate for 3 times
  7. washwashed with saturated saline
  8. customdried on sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified with a silica gel column chromatography

Sources & evidence

ORD record
ord-f83aeda1819848ee91395ddc9c0b4572
Source dataset
uspto-grants-2013_04
Patent number
US08426629B2

Reaction notes

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