Sodium Hydroxide → 4-(4-Chlorophenyl)-3-buten-2-one 2-oxime

HRID 567128Notes

Reaction equation

HRID 567128 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[C:10](=O)[CH3:11].[ClH:13].[NH2:14][OH:15].[OH-].[Na+]>CO>[Cl:13][C:6]1[CH:5]=[CH:4][C:3]([CH:8]=[CH:9][C:10](=[N:14][OH:15])[CH3:11])=[CH:2][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 5372820(E)-4-(2-Chloro-phenyl)-but-3-en-2-one

Product 1

HCID 48447934-(4-Chlorophenyl)-3-buten-2-one 2-oximeYield 54.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 250 ml single neck flask was charged 5.4 g (29.9 mmoles, 1.0 eq.) of (E)-4-(2-chlorophenyl)-3-buten-2-one and 5.2 g (75.4 mmoles, 2.5 eq) of hydroxylamine hydrochloride and 6 g of 50% sodium hydroxide (75 mmoles, 2.5 eq) and 100 ml of methanol. The reaction mixture was stirred at reflux for 2 hours. The reaction mixture was concentrated, diluted with water (50 ml), and then extracted with ethyl acetate (2×50 ml). The organic phase was dried and concentrated, to obtain 3.2 g of 4-(4-chlorophenyl)-3-buten-2-one 2-oxime (E/Z mixture of oxime isomers) as an oil in 54.7% yield.

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with water (50 ml)
  4. extractionextracted with ethyl acetate (2×50 ml)
  5. customThe organic phase was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d262abc5a847463ea9bc940d829aff99
Source dataset
uspto-grants-2001_01
Patent number
US06177462B1

Reaction notes

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