Acetone → 6-(4-Fluorophenyl)-3,5-hexadiene-2-one

HRID 971439Notes

Reaction equation

HRID 971439 reaction equation
[OH-].[Na+].[CH3:3][C:4]([CH3:6])=[O:5].[F:7][C:8]1[CH:17]=[CH:16][C:11]([CH:12]=[CH:13][CH:14]=O)=[CH:10][CH:9]=1.Cl>O.C(O)C>[F:7][C:8]1[CH:17]=[CH:16][C:11]([CH:12]=[CH:13][CH:14]=[CH:3][C:4](=[O:5])[CH3:6])=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 533843793-(4-Fluorophenyl)-2-propenal

Product 1

HCID 537516076-(4-Fluorophenyl)-3,5-hexadiene-2-oneYield 96.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Sodium hydroxide (2 g) in water (35 ml) was added to a stirred mixture of acetone (9.7 g) and ethanol (20 ml) cooled in a water bath. 4-Fluorocinnamaldehyde (5 g) was added dropwise to the stirred solution such that the temperature did not exceed 25°. The mixture was stirred at room temperature for 5 min, diluted with water (250 ml), adjusted to pH 1 with 5 M hydrochloric acid and extracted with ethyl acetate (3×100 ml). The combined extracts were washed with brine (1×100 ml), dried (MgSO4) and evaporated to give an orange oil (6.1 g) which was used crude in the next stage.

Workup

  1. temperaturecooled in a water bath
  2. customdid not exceed 25°
  3. extractionextracted with ethyl acetate (3×100 ml)
  4. washThe combined extracts were washed with brine (1×100 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-8b4c51753b58444ea4bfcfb81be36d79
Source dataset
uspto-grants-1979_07
Patent number
US04160036

Reaction notes

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