Hydrochloric Acid → 1-(2-Hydroxyphenyl)ethanone oxime
Reaction equation
[Cl-].[OH:2][NH3+:3].[C:4]([O-:7])(=O)[CH3:5].[Na+].O[CH2:10][C:11]([C:13]1C=C[CH:16]=[CH:15][CH:14]=1)=O.Cl>C(O)C.O>[OH:7][C:4]1[CH:5]=[CH:16][CH:15]=[CH:14][C:13]=1[C:11](=[N:3][OH:2])[CH3:10]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
Hydroxylammoniumchloride (6.96 g, 100 mmol) and sodium acetate.3H2O (13.6 g, 100 mmol) were dissolved in 150 mL ethanol:water (7:3) and added to a solution of 2-hydroxyacetophenone (6.81 g, 50 mmol) in 50 mL ethanol:water (7:3). The pH was adjusted to 4-5 with 4N HCl (˜10 mL) and the reaction mixture was then heated to reflux (100° C.) for 1 hour. The oil bath was removed and the mixture was left overnight with stirring. Ethanol was partly removed by evaporation and the aqueous phase was extracted with ethyl acetate two times. The combined organic phases were dried over magnesium sulphate and evaporated to dryness to produce 7.55 g of pure 24.
Workup
- temperaturethe reaction mixture was then heated
- customThe oil bath was removed
- customEthanol was partly removed by evaporation
- extractionthe aqueous phase was extracted with ethyl acetate two times
- dry with materialThe combined organic phases were dried over magnesium sulphate
- customevaporated to dryness
- customto produce 7.55 g of pure 24
Sources & evidence
- ORD record
- ord-276eed4d8fc94e64b8aa511ba6ef5ed0
- Source dataset
- uspto-grants-2003_09
- Patent number
- US06627645B2
Reaction notes
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