Acetic Acid → 1-(4-Fluorophenyl)-4-methylpent-1-en-3-one

HRID 1086815Notes

Reaction equation

HRID 1086815 reaction equation
[OH-].[K+].[F:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.[CH:12]([C:15]([CH3:17])=[O:16])([CH3:14])[CH3:13].C(O)(=O)C>CO.O>[F:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[CH:17][C:15](=[O:16])[CH:12]([CH3:14])[CH3:13])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 112513-Methyl-2-butanoneHCID 14797Potassium HydroxideHCID 680234-Fluorobenzaldehyde

Product 1

HCID 537214671-(4-Fluorophenyl)-4-methylpent-1-en-3-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

75 ml of 15% strength potassium hydroxide solution are added dropwise to 198.4 g (1.6 mol) of freshly distilled 4-fluorobenzaldehyde and 137.6 g (1.6 mol) of methyl isopropyl ketone in 300 ml of methanol and stirred overnight at room temperature. The mixture is then neutralized using 10 ml of acetic acid, 1 l of water is added and the mixture is extracted with two 500 ml portions of ether. The combined organic phases are washed with 500 ml of saturated sodium chloride solution and dried over sodium sulphate. After removing the solvent, the residue is distilled under high vacuum.

Workup

  1. additionis added
  2. extractionthe mixture is extracted with two 500 ml portions of ether
  3. washThe combined organic phases are washed with 500 ml of saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customAfter removing the solvent
  6. distillationthe residue is distilled under high vacuum

Sources & evidence

ORD record
ord-4d98f63a9a564ce38a461b260fab844f
Source dataset
uspto-grants-1991_07
Patent number
US05032590

Reaction notes

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