1-Chloromethylnaphthalene → (1-Naphthylmethyl)triphenylphosphonium chloride

HRID 2292867Notes

Reaction equation

HRID 2292867 reaction equation
[Cl:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[PH4+]>C(#N)C>[Cl-:1].[C:3]1([CH2:2][P+:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 68451-ChloromethylnaphthaleneHCID 11776TriphenylphosphineHCID 21584912Phosphanium chloride

Product 1

HCID 2734113(1-Naphthylmethyl)triphenylphosphonium chloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

340 g (1.93 mol) of 1-chloromethylnaphthalene (Aldrich) are dissolved together with 505.7 g (1.93 mol) of triphenylphosphine in 2 l of acetonitrile. The mixture is subsequently boiled at reflux with stirring for 5 hours. The phosphonium chloride begins to precipitate out after about 2 hours. The mixture is left to cool at room temperature and the crystals are filtered off with suction.

Workup

  1. temperatureat reflux
  2. customto precipitate out after about 2 hours
  3. waitThe mixture is left
  4. filtrationthe crystals are filtered off with suction

Sources & evidence

ORD record
ord-ba80841576e243baae5a16566386ab3e
Source dataset
uspto-grants-1997_11
Patent number
US05684185

Reaction notes

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