4-(2-Methyl-3-(4-chlorobenzoyl)phenyl)butanoic acid → HCID 21495671, compound

HRID 1731164Notes

Reaction equation

HRID 1731164 reaction equation
[CH3:1][O-:2].[K+].Cl[C:5]1[CH:25]=[CH:24][C:8]([C:9]([C:11]2[C:12]([CH3:23])=[C:13]([CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH:14]=[CH:15][CH:16]=2)=[O:10])=[CH:7][CH:6]=1>CO>[CH3:1][O:2][C:5]1[CH:25]=[CH:24][C:8]([C:9]([C:11]2[C:12]([CH3:23])=[C:13]([CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH:14]=[CH:15][CH:16]=2)=[O:10])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 1910664-(2-Methyl-3-(4-chlorobenzoyl)phenyl)butanoic acidHCID 23664618Potassium methoxide

Product 1

HCID 21495671HCID 21495671, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

17.5 g of 89% potassium methylate were added under an inert atmosphere to a suspension of 7.5 g of 4-(3'-p-chlorobenzoyl-2'-methyl-phenyl)-butyric acid (Example V) in 75 ml of methanol and was then heated at 120°-130° C for 17 hours under pressure. After cooling to room temperature, the mixture was rinsed with water and the methanol was eliminated under reduced pressure. The residue was dissolved in water, treated hot with activated carbon, iced and filtered. The filtrate was acidified to a pH of 1 with hydrochloric acid and the precipitate formed was recovered by filtration, was washed with water until the wash water was neutral and dried. The residue was crystallized from isopropyl ether to obtain 5.35 g of 4-(3'-p-methoxybenzoyl-2'-methyl-phenyl)-butyric acid in the form of colorless crystals melting at 100° C and then 115° C.

Workup

  1. temperaturewas then heated at 120°-130° C for 17 hours under pressure
  2. washthe mixture was rinsed with water
  3. dissolutionThe residue was dissolved in water
  4. additiontreated hot with activated carbon
  5. filtrationiced and filtered
  6. customthe precipitate formed
  7. filtrationwas recovered by filtration
  8. washwas washed with water until the wash water
  9. customdried
  10. customThe residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-b982dcc69d5e4b6795014530bd0c032f
Source dataset
uspto-grants-1976_11
Patent number
US03995056

Reaction notes

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