Ethyl Acrylate → HCID 19854199, compound

HRID 2427782Notes

Reaction equation

HRID 2427782 reaction equation
[Na].[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:12])[CH3:11])=[CH:5][CH:4]=1.[C:13](OCC)(=[O:16])[CH:14]=[CH2:15]>C(O)C.O>[F:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:15][CH2:14][C:13](=[O:16])[CH2:11][C:10]2=[O:12])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 8821Ethyl AcrylateHCID 521187(4-Fluorophenyl)acetoneHCID 5360545Sodium

Product 1

HCID 19854199HCID 19854199, compoundYield 10.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Sodium (0.3 g, 0.013 moles) was dissolved in ethanol (50 ml) and 4-Fluorophenylacetone (2.0 g, 0.013 moles) was added in ethanol (10 ml). Ethyl acrylate (1.3 g, 0.013 moles) was and the reaction mixture was heated at reflux overnight. The reaction mixture was allowed to cool and evaporated under reduced pressure to give a brown gum. Dissolved in water and washed with diethyl ether. The aqueous layer was acidified to pH2 with conc. Hydrochloric acid and extracted with dichloromethane. The extracts were combined and washed with water. Dried over anhydrous magnesium sulphate and filtered. The filtrate was evaporated to give an orange oil. (1.7 g) This was purified using a silica column eluted with dichloromethane:ethyl acetate 8:2 and then dichloromethane:ethyl acetate 2:1 to give a colorless gum. (0.428 g) This was triturated with diethyl ether/isohexane to give 4-(4-Fluorophenyl)cyclohexane-1,3-dione (0.28 g) as a white solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux overnight
  3. temperatureto cool
  4. customevaporated under reduced pressure
  5. customto give a brown gum
  6. washwashed with diethyl ether
  7. extractionextracted with dichloromethane
  8. washwashed with water
  9. dry with materialDried over anhydrous magnesium sulphate
  10. filtrationfiltered
  11. customThe filtrate was evaporated
  12. customto give an orange oil
  13. custom(1.7 g) This was purified
  14. washeluted with dichloromethane:ethyl acetate 8:2
  15. customdichloromethane:ethyl acetate 2:1 to give a colorless gum
  16. custom(0.428 g) This was triturated with diethyl ether/isohexane

Sources & evidence

ORD record
ord-c68ca76c51854f80bb259a26d16c726c
Source dataset
uspto-grants-2011_06
Patent number
US07968711B2

Reaction notes

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