Potassium Cyanide → HCID 68107449, compound

HRID 243810Notes

Reaction equation

HRID 243810 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N+:15]([O-:17])=[O:16])[C:8]([O:13][CH3:14])=[C:9]([CH2:11]Cl)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C-:18]#[N:19].[K+]>O1CCOCC1.C(O)C.O>[C:1]([C:5]1[CH:6]=[C:7]([N+:15]([O-:17])=[O:16])[C:8]([O:13][CH3:14])=[C:9]([CH2:11][C:18]#[N:19])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 68107643HCID 68107643, compound

Product 1

HCID 68107449HCID 68107449, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixed solution of 5-tert-butyl-1-(chloromethyl)-2-methoxy-3-nitrobenzene (1.93 g, 7.49 mmol) in dioxane (5.0 mL), ethanol (5.0 mL) and water (2.5 mL), potassium cyanide (0.980 g, 15.0 mmol) was added, and the mixture was stirred for 2 hours under reflux. After cooling the mixture to room temperature and evaporated under reduced pressure and water was added to the residue. The resultant was extracted with ethyl acetate and then dried over anhydrous sodium sulfate, evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=0/100-30/70) to obtain 1.84 g of the captioned compound (99% yield).

Workup

  1. temperatureunder reflux
  2. customevaporated under reduced pressure and water
  3. additionwas added to the residue
  4. extractionThe resultant was extracted with ethyl acetate
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=0/100-30/70)

Sources & evidence

ORD record
ord-9a496e5b775b4818a1c74b6a173bcacf
Source dataset
uspto-grants-2014_02
Patent number
US08653304B2

Reaction notes

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