Potassium Iodide → Benzoylethyl acetate

HRID 1966654Notes

Reaction equation

HRID 1966654 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[C:12]([O-:15])(=[O:14])[CH3:13].[Na+].[I-].[K+]>C(O)(=O)C.O>[C:12]([O:15][CH2:2][CH2:3][C:4](=[O:5])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 702953-ChloropropiophenoneHCID 517045Sodium Acetate

Product 1

HCID 11401278Benzoylethyl acetate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 3-chloro-1-phenylpropan-1-one (1.0 g, 5.93 mmol) in acetic acid (8 mL) was added sodium acetate (2.43 g, 29.7 mmol) and potassium iodide (100 mg). The mixture was heated in a sealed tube at 130° C. overnight. After cooling, the reaction was diluted with water (20 mL) and extracted with methylene chloride (3×20 mL). The combined organic extracts were washed with water (2×50 mL), saturated solution of sodium bicarbonate (2×50 mL) and brine (20 mL), dried (Na2SO4), and the solvent removed under reduced pressure. The title compound was obtained (1.0 g, 88%) as an orange solid.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with methylene chloride (3×20 mL)
  3. washThe combined organic extracts were washed with water (2×50 mL), saturated solution of sodium bicarbonate (2×50 mL) and brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-b10d795a98464716a008bc3d0354c66f
Source dataset
uspto-grants-2013_04
Patent number
US08420669B2

Reaction notes

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