Potassium Cyanide → HCID 66618771, compound

HRID 406383Notes

Reaction equation

HRID 406383 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([CH3:9])=[CH:4][C:3]=1[CH2:10]Cl.[C-:12]#[N:13].[K+].COC(C)(C)C>CS(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([CH3:9])=[CH:4][C:3]=1[CH2:10][C:12]#[N:13]

Participants

5

Reactant 3

HCID 9032Potassium Cyanide2×HCID 15413tert-Butyl methyl etherHCID 66618840HCID 66618840, compound

Product 1

HCID 66618771HCID 66618771, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1,5-dichloro-2-chloromethyl-4-methylbenzene (CAS #101349-87-5, 5.22 g) in dimethyl sulfoxide (20 ml) was added potassium cyanide (1.36 g) and the reaction solution was stirred at room temperature for 6 hours. Potassium cyanide (0.68 g) was added to the reaction solution and the solution was further stirred at room temperature overnight. To the reaction solution were added ice-cold water and tert-butyl methyl ether and the organic layer was separated. The water layer was re-extracted by the tert-butyl methyl ether. The combined organic layer was sequentially washed with water (twice) and brine. After drying over anhydrous magnesium sulfate, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (carrier: Walcogel™ C-200; elution solvent:heptane:ethyl acetate 49:1→19:1) to obtain the title compound (1.88 g). The property values of the obtained compound are as follows; 1H-NMR (CDCl3) δ (ppm): 2.38 (s, 3H), 3.78 (s, 2H), 7.38 (s, 1H), 7.43 (s, 1H).

Workup

  1. stirringthe solution was further stirred at room temperature overnight
  2. customthe organic layer was separated
  3. extractionThe water layer was re-extracted by the tert-butyl methyl ether
  4. washThe combined organic layer was sequentially washed with water (twice) and brine
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. concentrationthe organic layer was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (carrier: Walcogel™ C-200; elution solvent:heptane:ethyl acetate 49:1→19:1)

Sources & evidence

ORD record
ord-acab226b5b0d455c9012168dd7d0909a
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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