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

HRID 2399645

Reaktionsgleichung

Reaktionsgleichung von HRID 2399645
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

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) δ 0.89 (t, 9H), 1.43 (m, 12H), 2.52 (m, 6H), 4.41 (d, 2H), 4.88 (s, 2H), 7.33 (m, 2H), 7.45 (m, 1H), 7.52 (m, 1H).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f2a7d95f680842c6892208dfba32a576
Quelldatensatz
uspto-grants-1995_09
Patentnummer
US05451347

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