Water → 2-(2,4-dichlorophenoxy)benzaldehyde

HRID 397835Notes

Reaction equation

HRID 397835 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[Cl:18][C:19]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:20]=1[O:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[C:24]#N.[OH2:35]>C1COCC1>[Cl:18][C:19]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:20]=1[O:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH:24]=[O:35]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 27770202-(2,4-Dichlorophenoxy)benzonitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 27634272-(2,4-dichlorophenoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., a 1.2 M solution of diisobutylaluminum hydride in toluene (12.3 ml, 14.8 mmol) was added dropwise to a solution of 2-(2,4-dichlorophenoxy)benzonitrile (3.0 g, 11.3 mmol) in THF (30 ml). The reaction mixture was warmed to room temperature and stirred for 16 hours. It was cooled to 0° C. Water (10 ml) was added dropwise. It was warmed to room temperature. The solid was removed by filtration through a plug of celite. The solvent was removed from the filtrate in vacuo. The crude product was purified by flash chromatography on silica (130 g), using ethyl acetate/heptane 1:3 as eluent, to give 800 mg of 2-(2,4-dichlorophenoxy)benzaldehyde.

Workup

  1. temperatureIt was cooled to 0° C
  2. temperatureIt was warmed to room temperature
  3. customThe solid was removed by filtration through a plug of celite
  4. customThe solvent was removed from the filtrate in vacuo
  5. customThe crude product was purified by flash chromatography on silica (130 g)

Sources & evidence

ORD record
ord-0519b0b84fa64ff29b98496e1beb551c
Source dataset
uspto-grants-2003_08
Patent number
US06610721B2

Reaction notes

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