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

HRID 567135

Reaction equation

HRID 567135 reaction equation
[C:1]1([CH3:12])[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][C:9](=O)[CH3:10])=[CH:3][CH:2]=1.Cl.[NH2:14][OH:15].[OH-].[Na+]>CO>[C:1]1([CH3:12])[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][C:9](=[N:14][OH:15])[CH3:10])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 1073884-(4-Methylphenyl)-3-buten-2-oneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 738390244-(p-Tolyl)-3-buten-2-one 2-oximeYield 60.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 250 ml single neck flask was charged 4.8 g (30.0 mmoles, 1.0 eq.) of 4-(p-tolyl)-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-(p-tolyl)-3-buten-2-one 2-oxime (E/Z mixture of isomers) as an oil in 60.9% 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-e8e77fac645744bfa1e45fffba66d6dc
Source dataset
uspto-grants-2001_01
Patent number
US06177462B1

Linked notes

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