Trityl chloride → Triphenyl(triphenylmethyl)phosphonium chloride

HRID 274196Notes

Reaction equation

HRID 274196 reaction equation
[C:1]([Cl:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]1([P:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(#N)C>[Cl-:20].[C:34]1([P+:27]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:1]([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)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 11776Triphenylphosphine

Product 1

HCID 85420Triphenyl(triphenylmethyl)phosphonium chloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6.0 parts of trityl chloride was dissolved in 100 parts of acetonitrile and 5.7 parts of triphenylphosphine was added thereto. The mixture was heated under reflux for 6 hr. The mixture was allowed to stand for cooling and then the solvent was removed to obtain a brown oil which was then crystallized from acetone. The resulting crystals were collected by filtration and washed with acetone to obtain 9.2 parts of triphenyl(triphenylmethyl)phosphonium chloride (compound No. 69).

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 6 hr
  4. temperaturefor cooling
  5. customthe solvent was removed
  6. customto obtain a brown oil which
  7. customwas then crystallized from acetone
  8. filtrationThe resulting crystals were collected by filtration
  9. washwashed with acetone

Sources & evidence

ORD record
ord-f96ff1dae97348b5ba468c83d989122a
Source dataset
uspto-grants-1995_02
Patent number
US05389486

Reaction notes

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