Thionyl Chloride → 1-Methylcyclohexyl 2-(p-nitrophenyl)propionate

HRID 34537

반응식

HRID 34537 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:14])[C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH3:14])[C:11]([O:13][C:7]2([CH3:10])[CH2:8][CH2:9][CH2:4][CH2:5][CH2:6]2)=[O:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 892442-(4-Nitrophenyl)propionic acid

생성물 1

HCID 540684921-Methylcyclohexyl 2-(p-nitrophenyl)propionate수율 48%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

A stirred mixture of 97.5 g of 2-(p-nitrophenyl)-propionic acid [J. Med. Chem. Vol. 26, pages 222-226 (1983)], 40 ml of thionyl chloride and 500 ml of dry toluene was heated at 80° C. for 5 hours. The mixture was then allowed to cool and the solvent was evaporated under reduced pressure. The residual oil was dissolved in 400 ml of dry toluene, and 100 g of 1-methylcyclohexanol were added to the solution. The stirred mixture was heated at 80° C. for 1 hour and then at ambient temperature overnight. The solution was washed with 5% NaHCO3 solution, then water, dried over MgSO4 and finally evaporated to dryness. The crude mixture was purified over a column of 600 g of silica using CHCl3 as the eluant 34.95 g (24% yield) of 1-methyl-cyclohexyl 2-(p-nitrophenyl)-propionate as a golden yellow liquid.

후처리

  1. temperatureto cool
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residual oil was dissolved in 400 ml of dry toluene
  4. addition100 g of 1-methylcyclohexanol were added to the solution
  5. temperatureThe stirred mixture was heated at 80° C. for 1 hour
  6. customat ambient temperature
  7. customovernight
  8. washThe solution was washed with 5% NaHCO3 solution
  9. dry with materialwater, dried over MgSO4
  10. customfinally evaporated to dryness
  11. customThe crude mixture was purified over a column of 600 g of silica

출처 및 근거

ORD 기록
ord-48098c9e2ca7491bb519a9d866e60c5e
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04762840

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