Propanal → 3-(2,4-Dichlorophenyl)-2-methylpropenal

HRID 597888Notes

Reaction equation

HRID 597888 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[OH-].[K+].[CH:13](=[O:16])[CH2:14][CH3:15]>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[C:14]([CH3:15])[CH:13]=[O:16]

Participants

6

Reactant 3

HCID 527PropanalHCID 134042,4-DichlorobenzaldehydeHCID 14797Potassium Hydroxide

Product 1

HCID 724731863-(2,4-Dichlorophenyl)-2-methylpropenalYield 54.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

2,4-dichlorobenzaldehyde (26.26 g, 0.15 mol) was dissolved in toluene (200 mL), and then KOH (8.4 g, 1 eq) in water (183 mL) was added followed by BnEt3NCl. The mixture was cooled to 0° C. and n-propanal (26.15 g, 0.45 mol, 3 eq) in toluene (50 mL) was added dropwise. The mixture was allowed to warm to room temperature and stirred overnight. The organic layer was separated and washed successively with water, brine, dried (MgSO4), and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (0-1-2-3% EtOAc in hexanes) to give 17.56 g of 3-(2,4-dichlorophenyl)-2-methylpropenal.

Workup

  1. temperatureto warm to room temperature
  2. customThe organic layer was separated
  3. washwashed successively with water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (0-1-2-3% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4f4ea39e903644988b9e1e9e1e935ee1
Source dataset
uspto-grants-2011_03
Patent number
US07897601B2

Reaction notes

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