Triphenylphosphine → Hexyltriphenylphosphonium iodide

HRID 2399128Notes

Reaction equation

HRID 2399128 reaction equation
[C:1]1([P:7]([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.[I:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>C1(C)C(C)=CC=CC=1>[I-:20].[CH2:21]([P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 125271-Iodohexane

Product 1

HCID 10994370Hexyltriphenylphosphonium iodideYield 93.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 28.82 g of triphenylphosphine, 21.2 g of 1-iodo-hexane and 200 ml of xylene was refluxed for 5 hours and then was cooled. The solvent was decanted and the gummy residue was triturated with ether and dried at 90° to 100° C. under reduced pressure to obtain 44.53 g of n-hexyltriphenylphosphonium iodide melting at 106° C.

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperaturewas cooled
  3. customThe solvent was decanted
  4. customthe gummy residue was triturated with ether
  5. customdried at 90° to 100° C. under reduced pressure

Sources & evidence

ORD record
ord-6258c4f0ba694f10987cebffac7094b4
Source dataset
uspto-grants-1977_05
Patent number
US04027040

Reaction notes

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