Acetic Acid → HCID 53949022, compound

HRID 704748Notes

Reaction equation

HRID 704748 reaction equation
[OH-].[K+].[O:3]([C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[F:18])[CH:13]=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:19]([C:22]([CH3:24])=[O:23])([CH3:21])[CH3:20].C(O)(=O)C>CO.O>[F:18][C:17]1[CH:16]=[CH:15][C:12]([CH:13]=[CH:24][C:22](=[O:23])[CH:19]([CH3:21])[CH3:20])=[CH:11][C:10]=1[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 112513-Methyl-2-butanoneHCID 14797Potassium HydroxideHCID 1100684-Fluoro-3-phenoxybenzaldehyde

Product 1

HCID 53949022HCID 53949022, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

14.1 ml of 15% strength aqueous potassium hydroxide solution are added to 64.8 g (0.3 mol) of 3-phenoxy-4fluorobenzaldehyde and 51.6 g (0.6 mol) of methyl isopropyl ketone in 90 ml of methanol and the mixture is stirred overnight at room temperature. The mixture is neutralized using 1.95 ml of glacial acetic acid, diluted using 300 ml of water and extracted a number of times using ether. The organic phase is dried over magnesium sulphate and concentrated in vacuo, and the residue is chromatographed on a column (silica gel 70-230 mesh, using ethyl acetate/petroleum ether 1:9).

Workup

  1. additiondiluted
  2. extractionextracted a number of times
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customthe residue is chromatographed on a column (silica gel 70-230 mesh, using ethyl acetate/petroleum ether 1:9)

Sources & evidence

ORD record
ord-8c1166611d9244bf9165dc660c868102
Source dataset
uspto-grants-1991_01
Patent number
US04988711

Reaction notes

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