Isopropyl iodide → HCID 60644022, compound

HRID 1616542Notes

Reaction equation

HRID 1616542 reaction equation
I[CH:2]([CH3:4])[CH3:3].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([OH:15])=[C:10]([C:12](=[O:14])[CH3:13])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([O:15][CH:2]([CH3:4])[CH3:3])=[C:10]([C:12](=[O:14])[CH3:13])[CH:11]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 740613-Chloro-6-hydroxyacetophenone

Product 1

HCID 60644022HCID 60644022, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Add 2-iodopropane (63.3 mL, 633 mmol) dropwise to a suspension of 1-(5-chloro-2-hydroxyphenyl)ethanone (90.0 g, 528 mmol) and potassium carbonate (109.46 g, 792 mmol) in DMF (1000 mL) at room temperature under nitrogen and heat the mixture at 80° C. for 22 hours. Cool and filter the mixture and remove the solvent reduced pressure. Dilute the residue with ethyl acetate (1 L), wash with water (300 mL) and brine (200 mL), dry over sodium sulfate, and remove the solvent under reduced pressure to afford 1-(5-chloro-2-isopropoxyphenyl)ethanone (104.78 g, 93%).

Workup

  1. temperatureCool
  2. filtrationfilter the mixture
  3. customremove the solvent reduced pressure
  4. additionDilute the residue with ethyl acetate (1 L)
  5. washwash with water (300 mL) and brine (200 mL)
  6. dry with materialdry over sodium sulfate
  7. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-fb8bedf91bf546b282697ba0245c19b7
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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