Benzene, 1,3-bis(chloromethyl)- → 3-(Chloromethyl)benzyltri-n-butylphosphonium chloride

HRID 2399646

Reaction equation

HRID 2399646 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[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][Cl:23])[CH:17]=1>C1(C)C=CC=CC=1>[Cl-:14].[Cl:23][CH2:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=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 12275Benzene, 1,3-bis(chloromethyl)-HCID 13831Tributylphosphine

Product 1

HCID 676565363-(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-m-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, after which time the tri-n-butylphosphonium chloride salt had crystallized out of solution and TLC examination showed completion of reaction. The white crystals were filtered and washed several times with toluene and hexanes, and then dried. 1H NMR (CDCl3) δ 0.93 (t, 9H), 1.45 (m, 12H), 2.41 (m, 6H), 4.40 (d, 2H), 4.57 (s, 2H), 7.36 (m, 2H), 7.42 (d, 2H).

Workup

  1. customafter which time the tri-n-butylphosphonium chloride salt had crystallized out of solution and TLC examination
  2. customcompletion of reaction
  3. filtrationThe white crystals were filtered
  4. washwashed several times with toluene and hexanes
  5. customdried

Sources & evidence

ORD record
ord-ededb267cad641e9a7f04d2a0d38f761
Source dataset
uspto-grants-1995_09
Patent number
US05451347

Linked notes

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