Acetyl chloride → Methyl 4-oxo-1-phenylcyclohexanecarboxylate

HRID 966975노트

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HRID 966975 반응식
[C:1](Cl)(=O)C.[O:5]=[C:6]1[CH2:11][CH2:10][C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:12]([OH:14])=[O:13])[CH2:8][CH2:7]1.C(=O)([O-])O.[Na+]>CO>[O:5]=[C:6]1[CH2:11][CH2:10][C:9]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:12]([O:14][CH3:1])=[O:13])[CH2:8][CH2:7]1

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 3438864-Oxo-1-phenylcyclohexane-1-carboxylic acidHCID 516892Sodium Bicarbonate

생성물 1

HCID 10775931Methyl 4-oxo-1-phenylcyclohexanecarboxylate수율 98.1%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
45 °C

실험 절차

Acetyl chloride (0.46 mL, 0.50 g, 6.4 mmol) was added to a solution of 4-oxo-1-phenylcyclohexanecarboxylic acid (Description 2, 0.94 g, 4.3 mmol) in methanol (5 mL) and the mixture was heated under reflux for 20 hours. The mixture was cooled, poured into aqueous sodium hydrogen carbonate (saturated, 100 mL) and extracted with ethyl acetate (2×50 mL). The combined organic fractions were dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was dissolved in tetrahydrofuran (2 mL), acetic acid (6 mL) and water (2 mL) were added and the mixture was stirred at 45° C. for 2 hours. The mixture was cooled, the solvent was evaporated under reduced pressure and aqueous sodium hydrogen carbonate (saturated, 100 mL) was added. The mixture was extracted with ethyl acetate (2×50 mL), the combined organic fractions were dried (Na2SO2) and the solvent was evaporated under reduced pressure to give the tide compound (0.98 g, 98%). 1H NMR (250 MHz, CDCl3) δ 7.45-7.26 (5H, m), 3.72 (3H, s), 2.77 (2H, m), 2.61-2.38 (4H, m), and 2.25 (2H, m).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 20 hours
  3. temperatureThe mixture was cooled
  4. extractionextracted with ethyl acetate (2×50 mL)
  5. dry with materialThe combined organic fractions were dried (Na2SO4)
  6. customthe solvent was evaporated under reduced pressure
  7. dissolutionThe residue was dissolved in tetrahydrofuran (2 mL)
  8. additionacetic acid (6 mL) and water (2 mL) were added
  9. temperatureThe mixture was cooled
  10. customthe solvent was evaporated under reduced pressure and aqueous sodium hydrogen carbonate (saturated, 100 mL)
  11. additionwas added
  12. extractionThe mixture was extracted with ethyl acetate (2×50 mL)
  13. dry with materialthe combined organic fractions were dried (Na2SO2)
  14. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-cbe1b7dae01e47b7b8149ce4da63d56c
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06953792B2

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