Toluene → 1-Chloro-2-[(2-methylphenyl)methyl]benzene

HRID 1194559Notes

Reaction equation

HRID 1194559 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][C:5]1[CH:10]=[C:9](C(C)(C)C)[CH:8]=[CH:7][C:6]=1[CH3:15].ClC1C=CC=CC=1CC1C=CC(C(C)(C)C)=CC=1C.C1(C)C=CC=CC=1>[Fe](Cl)(Cl)Cl>[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:15]

Participants

5

Reactant 3

HCID 1140TolueneHCID 13593643HCID 13593643, compoundHCID 21270534HCID 21270534, compound

Product 1

HCID 135936451-Chloro-2-[(2-methylphenyl)methyl]benzeneYield 15.7%

Reagents, catalysts & solvents 1

HCID 24380Iron chloride (FeCl3)Catalyst

Conditions

Temperature
50 °C

Procedure

3.49 g (10.00 mmol) of an isomeric mixture comprising 45% of 2-(2-chlorobenzyl)-4-tert.-butyl-toluene and 55% of 2-(2-chlorobenzyl)-5-tert.-butyltoluene (total content of both isomers in the charge material: 78%), 9.2 g (100.00 mmol) of toluene, dried, and 0.8 g (5.00 mmol) of anhydrous, sublimed iron(III) chloride were placed in a flask, fitted with magnetic stirrer and reflux condenser. The mixture was stirred for 6 h at 50° C. The mixture (13.5 g) was then cooled to room temperature and analyzed by gas chromatography. 15.7% of 2-(2-chlorobenzyl)toluene (corresponding to the theoretical yield) could be detected as the only diphenylmethane derivative.

Workup

  1. customfitted with magnetic stirrer
  2. temperaturereflux condenser

Sources & evidence

ORD record
ord-24a0c37c0d1144e4a8f3b8c47a5cd23c
Source dataset
uspto-grants-1989_03
Patent number
US04814483

Reaction notes

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