2-Ethylbutyraldehyde → 2-(4-Chlorobenzyl)-2-ethylbutanal

HRID 1195668Notes

Reaction equation

HRID 1195668 reaction equation
[OH-].[Na+].[CH2:3]([CH:5]([CH2:8][CH3:9])[CH:6]=[O:7])[CH3:4].[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Cl)=[CH:13][CH:12]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][C:5]([CH2:8][CH3:9])([CH2:3][CH3:4])[CH:6]=[O:7])=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 73592-EthylbutyraldehydeHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14798Sodium Hydroxide

Product 1

HCID 151008312-(4-Chlorobenzyl)-2-ethylbutanal

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 1140TolueneSolvent2×

Procedure

300 ml of toluene, 400 ml of 30 percent (by weight) sodium hydroxide solution and 5.0 g of tetra-n-butylammonium iodide are heated at 80° C. while stirring. To this is slowly added dropwise a mixture of 110 g (1.10 mol) of 2-ethylbutanal and 161 g (1.00 mol) of 4-chlorobenzyl chloride. The mixture is then stirred at 80° C. for 4 h and at room temperature for 14 h, 1,000 ml of toluene are added, and the phases are separated. The organic phase is washed with water, dried over Na2SO4 and concentrated. Fractional distillation results in 123 g (54% of theory) of 2-(4-chlorobenzyl)-2-ethylbutanal as a colorless liquid of boiling point 146°-148° C. at 1 mbar.

Workup

  1. additionTo this is slowly added dropwise
  2. stirringThe mixture is then stirred at 80° C. for 4 h and at room temperature for 14 h
  3. customthe phases are separated
  4. washThe organic phase is washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. distillationFractional distillation
  8. customresults in 123 g (54% of theory) of 2-(4-chlorobenzyl)-2-ethylbutanal as a colorless liquid of boiling point 146°-148° C. at 1 mbar

Sources & evidence

ORD record
ord-ccc78cb1c752479d8f631238d7a0f7d9
Source dataset
uspto-grants-1992_05
Patent number
US05112828

Reaction notes

Loading…