Triphenylphosphine → [1,4-Phenylenebis(methylene)]bis(triphenylphosphanium) dichloride

HRID 2232159Notes

Reaction equation

HRID 2232159 reaction equation
[C:1]1([CH2:9]Cl)[CH:6]=[CH:5][C:4]([CH2:7][Cl:8])=[CH:3][CH:2]=1.[C:11]1([P:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CN(C)C=O>[CH:27]1[CH:26]=[CH:25][C:24]([P+:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:9][C:1]2[CH:6]=[CH:5][C:4]([CH2:7][P+:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[CH:3][CH:2]=2)=[CH:29][CH:28]=1.[Cl-:8].[Cl-:8]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 12171alpha,alpha'-Dichloro-p-xylene

Product 1

HCID 168940[1,4-Phenylenebis(methylene)]bis(triphenylphosphanium) dichlorideYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 175 ml of dimethylformamide were dissolved 1,513 g of p-xylylene dichloride and 50 g of triphenylphosphine and they were reacted for 3 hours under refluxing. Thereafter, the reaction mixture was cooled to room temperature, washed twice with each 100 ml of dimethylformamide and then washed twice with each 100 ml of diethyl ether, and then dried under reduced pressure to provide white powdery p-xylylenebis(triphenylphosphonium chloride) (XTPPC) having the following structure at a yield of 90%. ##STR13##

Workup

  1. customwere reacted for 3 hours
  2. temperatureunder refluxing
  3. washwashed twice with each 100 ml of dimethylformamide
  4. washwashed twice with each 100 ml of diethyl ether
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-b4b054c15a664dcc8bbc6a3d73fe76cd
Source dataset
uspto-grants-1988_11
Patent number
US04786709

Reaction notes

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