Hydrochloric Acid → 1-Octyl-2,4,6-trimethylbenzene

HRID 52765

Reaction equation

HRID 52765 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([CH3:13])[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[CH:6]=1.Cl[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].Cl>O>[CH2:15]([C:6]1[C:7]([CH3:12])=[CH:8][C:9]([CH3:11])=[CH:10][C:5]=1[CH3:13])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7947MesityleneHCID 81421-ChlorooctaneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 199638861-Octyl-2,4,6-trimethylbenzeneYield 34.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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.

Workup

  1. extractionextracted with toluene
  2. customThe organic phase is isolated
  3. concentrationconcentrated on a rotary evaporator
  4. customto give, at 88°-92° C.

Sources & evidence

ORD record
ord-5aec6e135de84d3e8073ee25308a0747
Source dataset
uspto-grants-1997_04
Patent number
US05616787

Linked notes

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