Hydrochloric Acid → HCID 86748894, compound

HRID 1779734Notes

Reaction equation

HRID 1779734 reaction equation
[OH-].[K+].[N:3](OCCCC)=[O:4].[CH3:10][C:11]1[CH:27]=[CH:26][CH:25]=[CH:24][C:12]=1[O:13][CH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[CH2:17][C:18]#[N:19].Cl>CC(C)=O>[OH:4][N:3]=[C:17]([C:18]#[N:19])[C:16]1[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=1[CH2:14][O:13][C:12]1[CH:24]=[CH:25][CH:26]=[CH:27][C:11]=1[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10996Butyl nitriteHCID 14797Potassium HydroxideHCID 19050196HCID 19050196, compound

Product 1

HCID 86748894HCID 86748894, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Acetone (5 ml), 85% potassium hydroxide (powder)(0.40 g, 6 mmol) and butyl nitrite (0.62 g, 6 mmol) were added to 2-(2-methylphenoxymethyl)benzyl cyanide (1.19 g, 5 mmol). The mixture was stirred at room temperature for 1 hour. After completion of the reaction, 1N aqueous hydrochloric acid solution (100 ml) was added. The mixture was extracted with toluene (100 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane/chloroform) to give α-hydroxyimino-2-(2-methylphenoxymethyl)benzyl cyanide (1.23 g, Yield: 92.4%, E/Z=35/65) as colorless crystals.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with toluene (100 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/chloroform)

Sources & evidence

ORD record
ord-b00a4a3450ba475b889eaef1b1c3ff5b
Source dataset
uspto-grants-1997_05
Patent number
US05627284

Reaction notes

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