Sodium Hydroxide → HCID 12853039, compound

HRID 2057992Notes

Reaction equation

HRID 2057992 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][C:12](=[O:14])[CH:11]=[C:10]([CH3:15])[CH:9]1C(OCC)=O.[OH-].[Na+]>C(O)C.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][C:12](=[O:14])[CH:11]=[C:10]([CH3:15])[CH2:9]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 12853038HCID 12853038, compound

Product 1

HCID 12853039HCID 12853039, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To 5-(2-fluorophenyl)-3-methyl-4-carbethoxy-2-cyclohexen-1-one (57.3 g, 0.21 mole) was added a solution of sodium hydroxide (11.5 g, 0.29 mole) in 35 ml of ethanol and 80 ml of water. The stirred reaction mixture was heated under reflux for 8 hours. The ethanol was removed by evaporation under reduced pressure, and the residue was extracted with diethyl ether. The ether extract was dried over sodium sulfate and filtered. The filtrate was evaporated under reduced pressure to give 5-(2-fluorophenyl)-3-methyl-2-cyclohexen-1-one (42.3 g).

Workup

  1. customThe stirred reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 8 hours
  4. customThe ethanol was removed by evaporation under reduced pressure
  5. extractionthe residue was extracted with diethyl ether
  6. extractionThe ether extract
  7. dry with materialwas dried over sodium sulfate
  8. filtrationfiltered
  9. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b864f76a026444069879d65c5def32a5
Source dataset
uspto-grants-1980_07
Patent number
US04214004

Reaction notes

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