Benzoyl chloride → cyanomethyl benzoate

HRID 2036122Notes

Reaction equation

HRID 2036122 reaction equation
[OH-].[Na+].[OH:3][CH2:4][C:5]#[N:6].[C:7](Cl)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(OCC)(=O)C>[C:7]([O:3][CH2:4][C:5]#[N:6])(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 7857HydroxyacetonitrileHCID 14798Sodium Hydroxide

Product 1

HCID 277773cyanomethyl benzoateYield 75%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Aqueous sodium hydroxide solution (4N, 60 mL) was added to aqueous hydroxyacetonitrile solution (52%, 25 g), and benzoyl chloride (25 mL) was slowly added dropwise under ice-cooling. After warming to room temperature, the mixture was stirred at room temperature overnight. Ethyl acetate was added to the solvent, and the mixture was washed with saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over sodium sulfate, and the residue was purified by silica gel column chromatography to give the object product (27.5 g, 75%).

Workup

  1. additionwas slowly added dropwise under ice-
  2. temperaturecooling
  3. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c574c319d3f148cfb1e16d47ccc4b21a
Source dataset
uspto-grants-2013_11
Patent number
US08575167B2

Reaction notes

Loading…