Acetyl chloride → Methyl 4-oxo-1-phenylcyclohexanecarboxylate

HRID 966975Notes

Reaction equation

HRID 966975 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-cbe1b7dae01e47b7b8149ce4da63d56c
Source dataset
uspto-grants-2005_10
Patent number
US06953792B2

Reaction notes

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