Acetone → HCID 53942944, compound

HRID 2372250Notes

Reaction equation

HRID 2372250 reaction equation
[OH-:1].[Na+].[CH2:3](O)C.C[C:7]([C:9]1[CH:14]=[CH:13][C:12](O)=[C:11]([F:16])[CH:10]=1)=O.[CH2:17](Br)[CH2:18][CH2:19][CH2:20][CH2:21]CCC.[CH3:26][C:27]([CH3:29])=[O:28]>O>[F:16][CH:11]([CH:12]([O:1][CH2:26][C:27]([C:29]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:28])[CH2:13][CH2:14][CH2:9][CH3:7])[CH2:10][CH3:3]

Participants

7

Reactant 5

HCID 180AcetoneHCID 702EthanolHCID 81401-BromooctaneHCID 14798Sodium HydroxideHCID 27373251-(3-Fluoro-4-hydroxyphenyl)ethan-1-one

Product 1

HCID 53942944HCID 53942944, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After 1.70 g of sodium hydroxide was dissolved in 13 ml of water, 26 ml of ethanol and 5.10 g of 3-fluoro-4-hydroxyacetophenone were added and stirred under heating to form a homogeneous solution, and then 7.41 g of octylbromide was added thereto with stirring under heating. After the heating under reflux for 1 hour, 15 ml of acetone was added and then the heating was continued under reflux for 13 hours. After acetone and ethanol were distilled off, the reaction mixture was poured into 80 ml of water. After the extraction with ether was repeated three times, the organic layers were gathered, washed with water and dried on magnesium sulfate. After magnesium sulfate was filtered off, the filtrate was concentrated and dried under a reduced pressure to obtain 7.45 g of a slightly brown crystal. This crystal was recrystallized with a mixed solvent of methanol and water to obtain 5.07 g (yield: 58%) of a white crystal having a melting point of 39.6°-40.1° C.

Workup

  1. temperatureunder heating
  2. customto form a homogeneous solution
  3. stirringwith stirring
  4. temperatureunder heating
  5. temperatureAfter the heating under reflux for 1 hour
  6. temperatureunder reflux for 13 hours
  7. distillationAfter acetone and ethanol were distilled off
  8. additionthe reaction mixture was poured into 80 ml of water
  9. extractionAfter the extraction with ether
  10. washwashed with water
  11. customdried on magnesium sulfate
  12. filtrationAfter magnesium sulfate was filtered off
  13. concentrationthe filtrate was concentrated
  14. customdried under a reduced pressure
  15. customto obtain 7.45 g of a slightly brown crystal
  16. customThis crystal was recrystallized with a mixed solvent of methanol and water

Sources & evidence

ORD record
ord-efd02ef9d4994f5ab9451953027b2ef2
Source dataset
uspto-grants-1992_03
Patent number
US05098602

Reaction notes

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