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

HRID 704743Notes

Reaction equation

HRID 704743 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 the mixture is stirred overnight at room temperature. It is then neutralized using 10 ml of acetic acid, 1 l of water is added and the mixture is extracted using 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 stripping off the solvent, the residue is distilled in a high vacuum.

Workup

  1. additionis added
  2. extractionthe mixture is extracted
  3. washThe combined organic phases are washed with 500 ml of saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. distillationthe residue is distilled in a high vacuum

Sources & evidence

ORD record
ord-9773d333a19e499ca576a1866e57fa31
Source dataset
uspto-grants-1991_01
Patent number
US04988711

Reaction notes

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