Acetic Acid → 2,4,6-Triethylbenzyl chloride

HRID 1890231Notes

Reaction equation

HRID 1890231 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH2:9][CH3:10])[CH:6]=[C:5]([CH2:11][CH3:12])[CH:4]=1)[CH3:2].CO[CH2:15][Cl:16].C(O)(=O)C>O>[CH2:11]([C:5]1[CH:6]=[C:7]([CH2:9][CH3:10])[CH:8]=[C:3]([CH2:1][CH3:2])[C:4]=1[CH2:15][Cl:16])[CH3:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 76021,3,5-TriethylbenzeneHCID 7864Chloromethyl Methyl Ether

Product 1

HCID 667076262,4,6-Triethylbenzyl chlorideYield 64.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 81.1 g of 1,3,5-triethylbenzene, 60.4 g of chloromethyl methyl ether and 6.0 g of acetic acid was stirred in a sealed tube at 120° C. for 7 hours. The reaction mixture was poured into 500 ml of water and extracted with hexane. The organic layer was washed with an aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate and then concentrated. The residue was distilled under reduced pressure to obtain 68.07 g of 2,4,6-triethylbenzyl chloride. Boiling point: 88 to 98° C. (0.18 kPa).

Workup

  1. extractionextracted with hexane
  2. washThe organic layer was washed with an aqueous sodium bicarbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-f1dff7138b904f85894adc23700a938f
Source dataset
uspto-grants-2013_08
Patent number
US08507410B2

Reaction notes

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