Chloroacetonitrile → Methyl 3-(cyanomethoxy)benzoate

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.

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

ORDレコード

ord-245287154a4a4f76a72ae555647e9fd1

出典データセット

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05981559