1,2-Bis(chloromethyl)benzene → 2-(Chloromethyl)benzyltri-n-butylphosphonium chloride

HRID 375019

Reaction equation

HRID 375019 reaction equation
[CH2:1]([P:5]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[Cl:14][CH2:15][C:16]1[C:17]([CH2:22][Cl:23])=[CH:18][CH:19]=[CH:20][CH:21]=1>C1(C)C=CC=CC=1>[Cl-:14].[Cl:23][CH2:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:15][P+:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:1][CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 119191,2-Bis(chloromethyl)benzeneHCID 13831Tributylphosphine

Product 1

HCID 676562342-(Chloromethyl)benzyltri-n-butylphosphonium chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of tri-n-butylphosphine (18.9 g, 103.8 mmol) in toluene (50 mL) was added dropwise to a mixture of α,α'-dichloro-o-xylene (7.0 g, 34.6 mmol) in toluene (200 mL) under argon gas. The reaction mixture was allowed to stir for several days at room temperature under argon, at which time TLC examination showed completion of reaction. Toluene was removed under reduced pressure to give an oily residue. The above oily residue was washed with toluene/hexane (50/50 (v/v), 4×100 mL), and then dried to give a colorless oil. 1H NMR (CDCl3) δ0.89 (t, 9H), 1.43 (m, 12H), 2.52 (m, 6H), 4.41 (d, 2H), 4.88 (s, 2H), 7.33 (m, 2H), 7.4 5 (m, 1H), 7.52 (m, 1H).

Workup

  1. customcompletion of reaction
  2. customToluene was removed under reduced pressure
  3. customto give an oily residue
  4. washThe above oily residue was washed with toluene/hexane (50/50 (v/v), 4×100 mL)
  5. customdried
  6. customto give a colorless oil

Sources & evidence

ORD record
ord-99457bcc819f4162b682d7924cdf7a88
Source dataset
uspto-grants-1996_01
Patent number
US05484556

Linked notes

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