M-Cresol → HCID 18407237, compound

HRID 1016560Notes

Reaction equation

HRID 1016560 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].[CH:18]1[C:23]([OH:24])=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:25]>CN(C)C=O>[C:19]1([CH3:25])[CH:20]=[CH:21][CH:22]=[C:23]([O:24][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[C:7](=[O:11])[CH2:6][CH2:5]3)[CH:18]=1

Participants

5

Reactant 3

HCID 342M-CresolHCID 11430Potassium CarbonateHCID 1365375-Fluoro-1-indanone

Product 1

HCID 18407237HCID 18407237, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

5 g of 5-fluoro-1-indanone are dissolved in 50 ml of dry dimethylformamide, and 18.2 g of anhydrous, powdered potassium carbonate and 3.57 g of m-cresol are added. The reaction mixture is stirred at 110° C. for 6 h. The solvent is removed by distillation in vacuo, and the residue is mixed with 100 ml of water and stirred for 2 h. The aqueous residue is extracted with ethyl acetate, and the organic extract is washed 3× with water, dried over sodium sulfate, filtered and concentrated in vacuo. 5-m-Tolyloxy-1-indanone is obtained as a brown oil which is reacted further without further purification.

Workup

  1. customThe solvent is removed by distillation in vacuo
  2. additionthe residue is mixed with 100 ml of water
  3. stirringstirred for 2 h
  4. extractionThe aqueous residue is extracted with ethyl acetate
  5. extractionthe organic extract
  6. washis washed 3× with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-72ff76b261cd449283f18a2b7b780b8e
Source dataset
uspto-grants-2002_11
Patent number
US06476059B1

Reaction notes

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