Sodium Hydroxide → HCID 86756285, compound

HRID 567130Notes

Reaction equation

HRID 567130 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11](=O)[CH3:12])[CH:6]=[CH:7][CH:8]=1.Cl.[NH2:17][OH:18].[OH-].[Na+]>CO>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11](=[N:17][OH:18])[CH3:12])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 1449341-[3-(Trifluoromethyl)phenyl]but-1-en-3-oneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 86756285HCID 86756285, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 250 ml single neck flask was charged 6.4 g (29.9 mmoles, 1.0 eq.) of 4-(3-trifluoromethylphenyl)-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 (50ml), and then extracted with ethyl acetate (2×50 ml). The organic phase was dried and concentrated, to obtain 4.4 g of 4-(3-trifluoromethylphenyl)-3-buten-2-one 2-oxime (E/Z mixture of isomers) as an oil in 64.2% yield.

Workup

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

Sources & evidence

ORD record
ord-2c499cc66140407898a7fae99f5a7e9e
Source dataset
uspto-grants-2001_01
Patent number
US06177462B1

Reaction notes

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