Sodium Hydroxide → HCID 12853039, compound

HRID 485529Notes

Reaction equation

HRID 485529 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-0a462799be99404aaa9d506f51ed3519
Source dataset
uspto-grants-1985_08
Patent number
US04536591

Reaction notes

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