Hydrochloric Acid → 3,3-Dimethyl-5-oxopentanoic acid

HRID 225027Notes

Reaction equation

HRID 225027 reaction equation
[CH3:1][C:2]([CH3:12])([CH2:9][CH:10]=[O:11])[CH2:3][C:4]([O:6]CC)=[O:5].[OH-].[K+].Cl>CO.O>[CH3:1][C:2]([CH3:12])([CH2:9][CH:10]=[O:11])[CH2:3][C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13050815Ethyl 4-formyl-3,3-dimethylbutanoate

Product 1

HCID 30187243,3-Dimethyl-5-oxopentanoic acidYield 83.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 1.50 g (8.71 mmol) of ethyl 3,3-dimethyl-5-oxopentanoate in 50 mL of methanol and 1 mL of water was added 1.0 g (17.8 mmol) of potassium hydroxide. The reaction mixture was stirred at room temperature for 411/2 hours. The reaction mixture was diluted with water and then made acidic by the addition of aqueous hydrochloric acid. The resulting solution was extracted with methylene chloride repeatedly. The combined organic layer was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. Removal of the solvent afforded 1.05 g of 3,3-dimethyl-5-oxopentanoic acid, 84% crude yield. The nmr spectrum was consistent with the proposed structure.

Workup

  1. extractionThe resulting solution was extracted with methylene chloride repeatedly
  2. washThe combined organic layer was washed with an aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-cdee1cd4a5c54003b3686ee464a9b13d
Source dataset
uspto-grants-1980_11
Patent number
US04235780

Reaction notes

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