Hydrochloric Acid → 4-Methyl-3-oxopentanoic acid

HRID 639698Notes

Reaction equation

HRID 639698 reaction equation
C([CH:3]([C:7](=[O:11])[CH:8]([CH3:10])[CH3:9])[C:4]([OH:6])=[O:5])C.Cl.[Cl-].[Na+]>[OH-].[Na+]>[CH3:9][CH:8]([CH3:10])[C:7](=[O:11])[CH2:3][C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 21016312Ethyl isobutyrylacetic acid

Product 1

HCID 4400244-Methyl-3-oxopentanoic acidYield 95.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Ethyl isobutyrylacetic acid (21 g, 132 mmol) was taken up in a 1.5M sodium hydroxide solution (15 g in 250 mL water) and stirred at room temperature over 16 h. The solution was cooled to 0° C. in an ice bath and was then acidified with 35 mL conc. Hydrochloric acid to pH 1-2. The resulting solution was saturated with sodium chloride and was then extracted with ethyl acetate (3×300 mL). The combined extracts were dried over sodium sulfate and then filtered and concentrated in vacuo to give the title compound as a clear oil (16.4 g, 95%).

Workup

  1. temperatureThe solution was cooled to 0° C. in an ice bath
  2. extractionwas then extracted with ethyl acetate (3×300 mL)
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5c875e3ec79a416cacae6863c3392570
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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