Sodium Hydroxide → 6-(4-Methylphenyl)-6-oxohexanoic acid

HRID 1720157Notes

Reaction equation

HRID 1720157 reaction equation
[OH-].[Na+].C[CH:4]([CH2:8][CH2:9][CH2:10][C:11](=[O:19])[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)[C:5]([OH:7])=[O:6]>CO>[CH3:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]([CH2:10][CH2:9][CH2:8][CH2:4][C:5]([OH:7])=[O:6])=[O:19])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22420412HCID 22420412, compound

Product 1

HCID 135988976-(4-Methylphenyl)-6-oxohexanoic acidYield 33.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Then, 1N sodium hydroxide (30 ml) is added to a solution of methyl 5-(4-methylbenzoyl)pentanoic acid (3.5 g) in methanol (100 ml) and the mixture heated under reflux for 5 hours. The methanol is removed in vacuo and water added to the residue. The resulting mixture is filtered and the filtrate acidified with 3N hydrochloric acid. The precipitate is collected by filtration and washed with water to provide 5-(4-methylbenzoyl)pentanoic acid (1.1 g) as colorless crystals, m.p. 147°-148° C. The structure is confirmed by NMR and 1R spectroscopy.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 5 hours
  3. customThe methanol is removed in vacuo and water
  4. additionadded to the residue
  5. filtrationThe resulting mixture is filtered
  6. filtrationThe precipitate is collected by filtration
  7. washwashed with water

Sources & evidence

ORD record
ord-df8f60d73ac846878e50c4e72e04a48c
Source dataset
uspto-grants-1996_04
Patent number
US05504244

Reaction notes

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