Sodium Hydroxide → HCID 287914, compound

HRID 567139Notes

Reaction equation

HRID 567139 reaction equation
[C:1]1([CH:11]=[CH:12]C(=O)C)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.[NH2:17][OH:18].[OH-].[Na+]>CO>[C:5]1([CH:4]=[CH:3][CH:2]=[CH:1][C:11](=[N:17][OH:18])[CH3:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 30177154-(1-Naphthalenyl)-3-buten-2-one

Product 1

HCID 287914HCID 287914, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 250 ml single neck flask was charged 5.28 g (30 mmoles, 1.0 eq.) of 4-(1-naphthyl)-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 3.4 of 4-(2-phenylethenyl)-3-buten-2one 2-oxime (E/Z mixture of isomers) as an oil in 60.6% 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-bbc76902b28942809b3a03a6dfa78123
Source dataset
uspto-grants-2001_01
Patent number
US06177462B1

Reaction notes

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