Chloroacetonitrile → Methyl 3-(cyanomethoxy)benzoate

HRID 1602495

반응식

HRID 1602495 반응식
[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]

참가 물질

5

반응물 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 88068Methyl 3-Hydroxybenzoate

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-245287154a4a4f76a72ae555647e9fd1
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05981559

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