Chloroacetonitrile → Methyl 3-(cyanomethoxy)benzoate

HRID 1602495

Reaktionsgleichung

Reaktionsgleichung von HRID 1602495
[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]

Komponenten

5

Edukt 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 88068Methyl 3-Hydroxybenzoate

Produkt 1

HCID 14917017Methyl 3-(cyanomethoxy)benzoateAusbeute 6.461 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-245287154a4a4f76a72ae555647e9fd1
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05981559

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