Reaction #81043

Reaction equation

HCl

aluminium chloride

mesitylene

1-chloroctane

→

title product

Yield 34.7%

1-octyl-2,4,6-trimethylbenzene

Yield 34.7%

Solvents

water

Conditions

Workup

1. 1
   Extractionextracted with toluene
2. 2
   OtherThe organic phase is isolated
3. 3
   Concentrationconcentrated on a rotary evaporator
4. 4
   Otherto give, at 88°-92° C.

Procedure

A 750 ml flask is charged with 6.7 g (50 mmol) of anhydrous aluminium chloride and 120.2 g (1 mol) of mesitylene. 148.7 g (1 mol) of 1-chloroctane are added dropwise to this mixture over 2 h at room temperature. HCl gas slowly evolves. The dark orange emulsion is stirred for c. 30 h at room temperature and then poured into water and extracted with toluene. The organic phase is isolated and concentrated on a rotary evaporator. The resultant oil is fractionated under vacuum to give, at 88°-92° C. and 1.8 mbar, 80.6 g of the title product as a colourless liquid. Gas chromatography (GC) and 1H-NMR spectrum analysis show that mono-n-octylmesitylene is obtained in 90% purity. The distillation residue contains mainly dioctylmesitylene.

Source