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

HRID 434585Notes

Reaction equation

HRID 434585 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 to pH 1 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, δ4.35 (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-20d8cced313942fd9c35261e118e5c5f
Source dataset
uspto-grants-1983_08
Patent number
US04398044

Reaction notes

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