Hydrochloric Acid → 2-Phenoxy-alpha-hydroxyiminobenzyl cyanide
Reaction equation
[Na].[O:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]#[N:17])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N:18](OCCC(C)C)=[O:19].Cl>C(O)C>[OH:19][N:18]=[C:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[O:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[C:16]#[N:17]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To anhydrous ethanol (15 ml) was dissolved sodium (0.55 g, 0.024 mole) and a mixture of 2-phenoxyphenylacetonitrile (4.18 g, 0.02 mole) and anhydrous ethanol (3 ml) was added dropwise to the mixture below 0° C. over 7 minutes. Isoamyl nitrite (3.51 g, 0.03 mole) was further added dropwise to the mixture below 0° C. over 10 minutes, followed by stirring at room temperature for 24 hours. After completion of the reaction, 5% hydrochloric acid was added to the reaction mixture, which was extracted with ether and dried over anhydrous magnesium sulfate. The crude product obtained by concentration under reduced pressure was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain α-hydroxyimino-2-phenoxyphenylacetonitrile (4.53 g, yield: 95.1%) as crystals having a low melting temperature.
Workup
- additionwas added dropwise to the mixture below 0° C. over 7 minutes
- additionwas added to the reaction mixture, which
- extractionwas extracted with ether
- dry with materialdried over anhydrous magnesium sulfate
- customThe crude product obtained by concentration under reduced pressure
- customwas purified by silica gel chromatography (ethyl acetate/n-hexane)
Sources & evidence
- ORD record
- ord-b1e68de080504a13b0f7949b1ba5595d
- Source dataset
- uspto-grants-1993_02
- Patent number
- US05183921
Reaction notes
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