3-Methyl-2-butanone → 1-(4-Fluorophenyl)-4-methylpent-1-en-3-one

HRID 1720742Notes

Reaction equation

HRID 1720742 reaction equation
[O-]CC.[Na+].[CH3:5][C:6]([CH:8]([CH3:10])[CH3:9])=[O:7].[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1>C(O)C.CCOCC>[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[CH:5][C:6](=[O:7])[CH:8]([CH3:10])[CH3:9])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 112513-Methyl-2-butanoneHCID 680234-FluorobenzaldehydeHCID 2723922Sodium ethoxide

Product 1

HCID 537214671-(4-Fluorophenyl)-4-methylpent-1-en-3-oneYield 53%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A sodium ethoxide solution (21% by weight in EtOH, 4.86 gm, 15 mmol) was added to a mixture of methylisopropylketone (8.61 gm, 100 mmol, from Aldrich) and 4-fluorobenzaldehyde (12.411 gm, 100 mmol, from Aldrich) in ethanol (150 ml). The solution was allowed to stir at room temperature for 3 hours. The solvent was evaporated to afford an orange oil. The oil was dissolved in ether, washed with saturated NH4Cl and brine, then dried over Na2SO4, filtered and concentrated to give an orange oil. The oil was purified by distillation (bp=106° C. at 1.3 mm Hg) to afford the title compound as a pale yellow oil (10.118 gm, 53%).

Workup

  1. customThe solvent was evaporated
  2. customto afford an orange oil
  3. washwashed with saturated NH4Cl and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an orange oil
  8. distillationThe oil was purified by distillation (bp=106° C. at 1.3 mm Hg)

Sources & evidence

ORD record
ord-553cf1aff0e543d1a185ffa7c57ce908
Source dataset
uspto-grants-1996_04
Patent number
US05506219

Reaction notes

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