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

HRID 66454Notes

Reaction equation

HRID 66454 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-52d90664584e4fd28beaef7c291c05f5
Source dataset
uspto-grants-1982_08
Patent number
US04342694

Reaction notes

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