Ethanol → 5-Ethyl-5-methyl-4-oxohept-2-enoic acid

HRID 648148Notes

Reaction equation

HRID 648148 reaction equation
C(O)C.[OH-].[K+].[Cl-].[Na+].[CH2:8]([C:10]([CH3:21])([CH2:19][CH3:20])[C:11](=[O:18])[CH2:12][CH:13](O)[C:14]([OH:16])=[O:15])[CH3:9]>O>[CH2:19]([C:10]([CH3:21])([CH2:8][CH3:9])[C:11](=[O:18])[CH:12]=[CH:13][C:14]([OH:16])=[O:15])[CH3:20]

Participants

6

Reactant 4

HCID 702EthanolHCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 204821255-Ethyl-2-hydroxy-5-methyl-4-oxoheptanoic acid

Product 1

HCID 544809195-Ethyl-5-methyl-4-oxohept-2-enoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The product of the preparation immediately above was dissolved in 400 ml. of ethanol and brought to a boil. To it was quickly added 40 g. of potassium hydroxide in 360 ml. of water, and the temperature was held at 72° for 2 minutes. The mixture was then poured immediately into 1 liter of ice-water, and 50 g. of sodium chloride was added. The aqueous mixture was extracted with 1000 ml. of diethyl ether, and the aqueous layer was made acid with concentrated hydrochloric acid. It was then extracted 4 times with 500 ml. portions of dichloromethane, and the organic layers were combined, dried over magnesium sulfate and evaporated under vacuum to obtain 20 g. of the desired acid, as a mixture with 5-ethyl-2-hydroxy-5-methyl-4-oxoheptanoic acid, the presence of which was indicated by nuclear magnetic resonance signals, δ 4.35 (q, 1H); 2.6-3.8 (m, 2H).

Workup

  1. customThe product of the preparation immediately
  2. dissolutionabove was dissolved in 400 ml
  3. extractionThe aqueous mixture was extracted with 1000 ml
  4. extractionIt was then extracted 4 times with 500 ml
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under vacuum
  7. customto obtain 20 g

Sources & evidence

ORD record
ord-0d74dd8485524c119c7e00775bb1f101
Source dataset
uspto-grants-1983_10
Patent number
US04411753

Reaction notes

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