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

HRID 375018

Reaction equation

HRID 375018 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 190321702-(Chloromethyl)benzyltriethylphosphonium chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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) δ1.15-1.26 (dt, 9), 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).

Workup

  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

Sources & evidence

ORD record
ord-10ae76f6ec0f4443944228377f5b406d
Source dataset
uspto-grants-1996_01
Patent number
US05484556

Linked notes

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