Hydrochloric Acid → 2-Phenoxy-alpha-hydroxyiminobenzyl cyanide

HRID 1756751Notes

Reaction equation

HRID 1756751 reaction equation
[OH-].[K+].[N:3](OCCCC)=[O:4].[O:10]([C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[CH2:19][C:20]#[N:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>O.C1(C)C=CC=CC=1>[O:10]([C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([C:20]#[N:21])=[N:3][OH:4])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10996Butyl nitriteHCID 14797Potassium HydroxideHCID 1412212-Phenoxyphenylacetonitrile

Product 1

HCID 853212152-Phenoxy-alpha-hydroxyiminobenzyl cyanideYield 78,002.102%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

85% Potassium hydroxide (3.96 g, 0.06 mol), toluene (100 ml) and butyl nitrite (6.19 g, 0.06 mmol) were added to 2-phenoxybenzyl cyanide (10.46 g, 0.05 mol). The mixture was stirred at room temperature for 16 hours. After completion of the reaction, water (100 ml) was added. The mixture was neutralized with hydrochloric acid, extracted with ether (150 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 2-phenoxy-α-hydroxyiminobenzyl cyanide (11.15 g, Yield: 93.6%, E/Z=11/89).

Workup

  1. additionwas added
  2. extractionextracted with ether (150 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-110de0b657cf41fbb17c21902e05528b
Source dataset
uspto-grants-1995_08
Patent number
US05442063

Reaction notes

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