Sodium Cyanide → HCID 13602723, compound

HRID 2101712Notes

Reaction equation

HRID 2101712 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C-]#N.[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[C:4]([CH:4]([C:3]1[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:2]=1[Cl:1])[OH:5])=[O:5]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 134042,4-Dichlorobenzaldehyde

Product 1

HCID 13602723HCID 13602723, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
105 °C

Procedure

To a mixture of 2,4-dichlorobenzaldehyde (5.0 gm, 29 mmol) in ethanol (10 mL) was added a solution of sodium cyanide (500 mg, 10 mmol) in water (5 mL). The reaction was heated to reflux (100-110° C.) for 1 hr and was then cooled, diluted with water, and extracted twice with ethyl acetate. The organic layers were washed with brine, dried over sodium sulfate, and evaporated. The residue was purified by flash chromatography (10% methylene chloride, 10% ethyl acetate in hexanes) to afford the title compound as an oil.

Workup

  1. temperatureThe reaction was heated
  2. temperaturewas then cooled
  3. extractionextracted twice with ethyl acetate
  4. washThe organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was purified by flash chromatography (10% methylene chloride, 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-63cc00c6b98a4d6e9f51c2354811bf3c
Source dataset
uspto-grants-2009_08
Patent number
US07572785B2

Reaction notes

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