Dimethyl Sulfate → 2-Phenoxy-alpha-methoxyiminobenzyl cyanide

HRID 1756753Notes

Reaction equation

HRID 1756753 reaction equation
[OH-].[Na+].[N:3]([O:5][CH2:6]CCC)=O.[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.S(OC)(OC)(=O)=O>O.CCOCC.CC(C)=O>[O:10]([C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([C:20]#[N:21])=[N:3][O:5][CH3:6])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

8

Reactant 4

HCID 6497Dimethyl SulfateHCID 10996Butyl nitriteHCID 14798Sodium Hydroxide2×HCID 1412212-Phenoxyphenylacetonitrile

Product 1

HCID 541653652-Phenoxy-alpha-methoxyiminobenzyl cyanideYield 93.6%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

95% sodium hydroxide (0.40 g, 6 mmol), acetone (10 ml) and butyl nitrite (0.62 g, 6 mmol) were added to 2-phenoxybenzyl cyanide (1.05 g, 5 mmol). The mixture was stirred at room temperature for 1.5 hours. Dimethyl sulfate (0.76 g, 6 mmol) was added, and the mixture was stirred at room temperature for 0.5 hours. After completion of the reaction, ether (10 ml) and 1N aqueous sodium hydroxide solution (10 ml) were added, and the mixture was stirred at room temperature for 0.5 hour. After stirring, water (100 ml) was added. The mixture was extracted with ether (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) to give 2-phenoxy-α-methoxyiminobenzyl cyanide (1.18 g, Yield: 93.5%, E/Z=23/77).

Workup

  1. stirringthe mixture was stirred at room temperature for 0.5 hours
  2. additionwere added
  3. stirringthe mixture was stirred at room temperature for 0.5 hour
  4. stirringAfter stirring
  5. extractionThe mixture was extracted with ether (100 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-325d4d7a89824d6ab37f72d734686979
Source dataset
uspto-grants-1995_08
Patent number
US05442063

Reaction notes

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