Hydrochloric Acid → 4-(2-Fluoro-5-methylphenyl)-3-buten-2-one

HRID 1700716Notes

Reaction equation

HRID 1700716 reaction equation
[OH-:1].[Na+].[F:3][C:4]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:5]=1[CH:6]=O.FC1C=CC(C)=[C:18]([CH:21]=1)[CH:19]=O.Cl>CC(C)=O.O>[F:3][C:4]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:5]=1[CH:6]=[CH:21][C:18](=[O:1])[CH3:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 27590125-Fluoro-2-methylbenzaldehydeHCID 32778232-Fluoro-5-methylbenzaldehyde

Product 1

HCID 539200784-(2-Fluoro-5-methylphenyl)-3-buten-2-one

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent3×HCID 962WaterSolvent

Procedure

To a mixture of acetone (160 ml), sodium hydroxide (6.4 g) and water (200 ml) was added dropwise at 0° C. a mixture of 2-fluoro-5-methylbenzaldehyde and 5-fluoro-2-methylbenzaldehyde (about 1:7) (28.1 g) in acetone (40 ml), and the mixture was stirred at the same temperature for 1 hour. To the mixture was added 1N hydrochloric acid (160 ml), and acetone was evaporated under reduced pressure. The residue was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate-hexane) to give 4-(2-fluoro-5-methylphenyl)-3-buten-2-one (18.2 g).

Workup

  1. additionwas added dropwise at 0° C.
  2. customwas evaporated under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate
  4. washthe organic layer was washed with water and saturated brine
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified with silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-e962c11f8a9f4af2a2fcc12d866f1b16
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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