Potassium Iodide → HCID 20093009, compound

HRID 274569Notes

Reaction equation

HRID 274569 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:16])[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:26][C:27]#[N:28]>CN(C=O)C>[C:27]([CH2:26][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:16])[C:9]1[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=1)#[N:28]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 29594Benzophenone, 2-hydroxy-4'-methyl-

Product 1

HCID 20093009HCID 20093009, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2'-hydroxy-4-methylbenzophenone (9 g), potassium iodide (8.46 g) and potassium carbonate (8.79 g) in DMF (200 ml) was added chloroacetonitrile (3.85 g) and the mixture was stirred at room temperature for 2 days. The reaction mixture was concentrated to dryness. After the addition of water, the mixture was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried and concentrated to dryness. The residue was purified by column chromatography on silica gel to give pale brown syrup (8.9 g, 84%).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. additionAfter the addition of water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c980f585d47740cba4eec916169230c1
Source dataset
uspto-grants-1995_02
Patent number
US05389641

Reaction notes

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