Sulfuric Acid → 3-(4-Fluorophenyl)-1-phenylprop-2-en-1-one

HRID 2295226Notes

Reaction equation

HRID 2295226 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[F:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.OS(O)(=O)=O.[OH-].[Na+]>CC(O)=O.O>[F:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[CH:2][C:1]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:3])=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 7410AcetophenoneHCID 14798Sodium HydroxideHCID 680234-Fluorobenzaldehyde

Product 1

HCID 982013-(4-Fluorophenyl)-1-phenylprop-2-en-1-oneYield 60.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of acetophenone (7.02 gm, 58.4 mmol), p-fluorobenzaldehyde (7.24 gm, 58.4 mmol) and concentrated H2SO4 (10 ml) in glacial HOAc (116 ml) was stirred at room temperature for 2 days. The solution was poured into H2O (250 ml) and neutralized with 10% NaOH (200 ml). The aqueous layer was extracted once with Et2O and the Et2O layer was washed successively with H2O, saturated NaHCO3 (twice) and brine, then dried (magnesium sulfate). Filtration and removal of the solvent afforded a yellow solid, which was recrystallized from hot hexane to give the title compound (7.94 gm, 60%) as light yellow needles.

Workup

  1. extractionThe aqueous layer was extracted once with Et2O
  2. washthe Et2O layer was washed successively with H2O, saturated NaHCO3 (twice) and brine
  3. dry with materialdried (magnesium sulfate)
  4. filtrationFiltration and removal of the solvent
  5. customafforded a yellow solid, which
  6. customwas recrystallized from hot hexane

Sources & evidence

ORD record
ord-806400b9aa284263bef9a9194bdb74c9
Source dataset
uspto-grants-1997_11
Patent number
US05691322

Reaction notes

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