Hydrochloric Acid → 2-(Ethoxycarbonyl)butanoic acid

HRID 80293

Reaction equation

HRID 80293 reaction equation
[CH2:1]([CH:3]([C:9]([O:11]CC)=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C(O)C.[OH-].[K+].Cl>O.C(OCC)C>[C:4]([CH:3]([CH2:1][CH3:2])[C:9]([OH:11])=[O:10])([O:6][CH2:7][CH3:8])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 8610Diethyl ethylmalonateHCID 14797Potassium Hydroxide

Product 1

HCID 108989792-(Ethoxycarbonyl)butanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Diethyl ethylmalonate was stirred overnight with 95% ethanol in the presence of 1M KOH. The white precipitate that forms was filtered out of solution, and the filtrate was concentrated under reduced pressure (e.g., on a rotary evaporator). The yellowish oil obtained upon concentration of the filtrate was added to the precipitate and the mixture was dissolved in a minimum amount of water. After acidification with dilute aqueous HCl to a pH of 2, an oil separates from the solution. The oil was taken up into diethyl ether and the aqueous layer was extracted three times with further with diethyl ether. The ether extracts were combined, dried over magnesium sulfate and filtered. A quantitative yield of 2-carboethoxybutyric acid was obtained as a yellowish oil.

Workup

  1. filtrationThe white precipitate that forms was filtered out of solution
  2. concentrationthe filtrate was concentrated under reduced pressure (e.g.
  3. customon a rotary evaporator)
  4. customThe yellowish oil obtained upon concentration of the filtrate
  5. additionwas added to the precipitate
  6. extractionthe aqueous layer was extracted three times with further with diethyl ether
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered

Sources & evidence

ORD record
ord-5eb28bacb9664f2fa52b58188a0537d2
Source dataset
uspto-grants-2014_09
Patent number
US08846021B2

Linked notes

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