Sulfuric Acid → 4-Fluorochalcone

HRID 1720689Notes

Reaction equation

HRID 1720689 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 53669884-FluorochalconeYield 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 (2×) and brine, then dried (MgSO4). Filtration and removal of the solvent afforded a yellow solid which was recrystallized from hot hexane to give (E)-3-(4-fluorophenyl)-1-phenyl-2-propen-1-one (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 (2×) and brine
  3. dry with materialdried (MgSO4)
  4. filtrationFiltration and removal of the solvent
  5. customafforded a yellow solid which
  6. customwas recrystallized from hot hexane

Sources & evidence

ORD record
ord-d80907f021884859b9a0b12c92ddd187
Source dataset
uspto-grants-1996_04
Patent number
US05506219

Reaction notes

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