Acetone → (E)-4-(2,4-difluorophenyl)but-3-en-2-one

HRID 1189549Notes

Reaction equation

HRID 1189549 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:11][C:12]([CH3:14])=[O:13].[OH-].[Na+]>O>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1/[CH:4]=[CH:11]/[C:12](=[O:13])[CH3:14]

Participants

5

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 737702,4-Difluorobenzaldehyde

Product 1

HCID 58310994(E)-4-(2,4-difluorophenyl)but-3-en-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2,4-difluorobenzaldehyde (5.0 ml, 45.7 mmol) and acetone (10.75 ml, 146 mmol) in Water (10 ml), was added 0.25M sodium hydroxide (18.30 ml, 4.57 mmol). The reaction mixture was heated to for 2 h. The mixture was poured into ice water. It was extracted with ethyl acetate (200 ml). The organic layer was dried, filtered, and evaporated to give (E)-4-(2,4-difluorophenyl)but-3-en-2-one as yellow oil. It was used for the next reaction without purification. 1H NMR (CDCl3/400 MHz): δ (ppm) 7.60 (d, 1H), 7.60-7.53 (m, 1H), 6.96-6.86 (m, 2H), 6.73 (d, 1H), 2.39 (s, 3H).

Workup

  1. temperatureThe reaction mixture was heated to for 2 h
  2. extractionIt was extracted with ethyl acetate (200 ml)
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-5185cd3713a448b7a379a6b0f8ac835b
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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