Sodium Hydroxide → 2-Ethyl-3-oxobutanoic acid

HRID 2245816Notes

Reaction equation

HRID 2245816 reaction equation
[OH-].[Na+].[CH2:3]([CH:5]([C:11]([CH3:13])=[O:12])[C:6]([O:8]CC)=[O:7])[CH3:4]>O>[CH2:3]([CH:5]([C:11]([CH3:13])=[O:12])[C:6]([OH:8])=[O:7])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 79065Butanoic acid, 2-ethyl-3-oxo-, ethyl ester

Product 1

HCID 204932-Ethyl-3-oxobutanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydroxide (1.92 g) was dissolved in water (10 mL) and ethyl 2-ethylacetoacetate (6.32 g: made by Wako Pure Chemical Industries) was added while stirring at room temperature, and this was further stirred for 30 minutes. The ethanol was subsequently removed with a rotary evaporator, and the remaining aqueous layer was washed with ether. To this was added ether (20 mL), and then, while stirring and chilling with ice, a solution of concentrated sulfuric acid 2.35 g dissolved in water 8 mL was added dropwise. The ether layer was fractioned off, and the aqueous layer was salt precipitated and extracted with ether. The ether layers were combined to yield an ether solution of α-ethylacetoacetic acid.

Workup

  1. stirringthis was further stirred for 30 minutes
  2. customThe ethanol was subsequently removed with a rotary evaporator
  3. washthe remaining aqueous layer was washed with ether
  4. additionTo this was added ether (20 mL)
  5. stirringwhile stirring
  6. temperaturechilling with ice
  7. dissolutiona solution of concentrated sulfuric acid 2.35 g dissolved in water 8 mL
  8. additionwas added dropwise
  9. customprecipitated
  10. extractionextracted with ether

Sources & evidence

ORD record
ord-ad7ca129e656475aa1d34dcf42b390b5
Source dataset
uspto-grants-2010_03
Patent number
US07683195B2

Reaction notes

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