Chloroacetonitrile → Methyl 3-(cyanomethoxy)benzoate

HRID 1602495

Reaction equation

HRID 1602495 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:19][C:20]#[N:21]>CN(C)C=O>[C:20]([CH2:19][O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])#[N:21]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 14917017Methyl 3-(cyanomethoxy)benzoateYield 6,461%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3-hydroxybenzoate (10.00 g, 65.72 mmol) was dissolved in dimethylformamide (100 ml). With stirring the solution under ice-cooling, potassium carbonate (13.63 g, 98.58 mmol) and chloroacetonitrile (4.99 ml, 78.86 mmol) were added in that order, and the mixture was stirred at room temperature for 12 hours. The reaction solution was poured into ice-water and the crystals precipitated were collected by filtration. The resulting crystals were dissolved in chloroform, and the solution was washed with 5% potassium carbonate aqueous solution, 10% citric acid aqueous solution and brine in that order, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. By crystallizing the resulting residue from diethyl etherhexane, methyl 3-cyanomethoxybenzoate (811.80 g, 94%) was obtained.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 12 hours
  3. customthe crystals precipitated
  4. filtrationwere collected by filtration
  5. dissolutionThe resulting crystals were dissolved in chloroform
  6. washthe solution was washed with 5% potassium carbonate aqueous solution, 10% citric acid aqueous solution and brine in that order
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customBy crystallizing the resulting residue from diethyl etherhexane

Sources & evidence

ORD record
ord-245287154a4a4f76a72ae555647e9fd1
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Linked notes

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