Ethanol → 3-Phenylprop-2-ynal oxime

HRID 2040838Notes

Reaction equation

HRID 2040838 reaction equation
[C:1]1([C:7]#[C:8][CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:12][OH:13].CCO>O>[C:1]1([C:7]#[C:8][CH:9]=[N:12][OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 75740PhenylpropynalHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 765430553-Phenylprop-2-ynal oximeYield 100.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of phenylpropargylaldehyde (859 mg, 6.6 mmol), hydroxylamine hydrochloride (4.59 g, 66 mmol), EtOH (48 mL) and water (12 mL) was stirred at r.t. for 24 h. The reaction mixture was diluted with H2O, extracted with Et2O-EtOAc, washed with brine and evaporated to dryness in vacuo affording 0.96 g of the title compound (syn:anti 1:1) as a pasty brownish solid.

Workup

  1. extractionextracted with Et2O-EtOAc
  2. washwashed with brine
  3. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-e5b6604bca9d464cafbb0a7fe9a0e4c7
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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