Potassium Cyanide → 1091611-71-0

HRID 1747057Notes

Reaction equation

HRID 1747057 reaction equation
[C-:1]#[N:2].[K+].O1CCOCCOCCOCCOCCOCC1.Cl[CH2:23][C:24]1[CH:25]=[C:26]([CH:34]=[CH:35][CH:36]=1)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]>C(#N)C>[C:1]([CH2:23][C:24]1[CH:25]=[C:26]([CH:34]=[CH:35][CH:36]=1)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])#[N:2]

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 22456708tert-Butyl 3-(chloromethyl)benzoate

Product 1

HCID 594787811091611-71-0Yield 80.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a mixed liquid of 1.51 g of potassium cyanide and 70 ml of acetonitrile, 6.12 g of 1,4,7,10,13,16-hexaoxacyclooctadecane was added, followed by stirring for 2 hours. Thereafter, a solution of 5.00 g of tert-butyl 3-(chloromethyl)benzoate in 30 ml of acetonitrile was added thereto, followed by stirring at room temperature for 18 hours. The reaction solution was concentrated, diluted with diethyl ether-hexane (1:1), and then washed with water and a saturated aqueous sodium chloride solution. After drying over anhydrous magnesium sulfate, the solvent was evaporated, and the residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to obtain 3.86 g of tert-butyl 3-(cyanomethyl)benzoate as a colorless oily substance.

Workup

  1. stirringby stirring at room temperature for 18 hours
  2. concentrationThe reaction solution was concentrated
  3. additiondiluted with diethyl ether-hexane (1:1)
  4. washwashed with water
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-56ad47aff41d4a8585378095778ee40b
Source dataset
uspto-grants-2015_10
Patent number
US09150541B2

Reaction notes

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