1,2-Bis(chloromethyl)benzene → 2-(Chloromethyl)benzyltriethylphosphonium chloride

HRID 2399644Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2399644
[Cl:1][CH2:2][C:3]1[C:4]([CH2:9][Cl:10])=[CH:5][CH:6]=[CH:7][CH:8]=1.[CH2:11]([P:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[CH3:12].[Cl-].C([PH+](CC)CC)C>C1(C)C=CC=CC=1>[Cl-:1].[Cl:10][CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][P+:13]([CH2:16][CH3:17])([CH2:14][CH3:15])[CH2:11][CH3:12]

Komponenten

5

Edukt 3

HCID 119191,2-Bis(chloromethyl)benzeneHCID 27365TriethylphosphineHCID 19032181Triethylphosphonium chloride salt

Produkt 1

HCID 190321702-(Chloromethyl)benzyltriethylphosphonium chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of α,α'-dichloro-o-xylene (15.0 g, 86.0 mmol) in toluene (200 ml) was added triethylphosphine (6.3 ml, 43.0 mmol) under argon gas. The reaction mixture was stirred for several days at room temperature under argon after which time the triethylphosphonium chloride salt had crystallized out of solution. The crystals were filtered and washed with toluene (3×50 mL) and pentane (3×50 mL) and dried: 1H NMR (CDCl3) δ 1.15-1.26 (dt, 9H), 2.58-2.69 (m, 6H), 4.39-4.44 (d, 2H), 4.87 (s, 2H), 7.31-7.34 (dd, 2H), 7.43-7.46 (dd, 1H), 7.50-7.54 (m, 1H).

Aufarbeitung

  1. customhad crystallized out of solution
  2. filtrationThe crystals were filtered
  3. washwashed with toluene (3×50 mL) and pentane (3×50 mL)
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2aa949a129fb4878b6c20c993ac9046f
Quelldatensatz
uspto-grants-1995_09
Patentnummer
US05451347

Notizen zur Reaktion

Wird geladen…