Potassium Hydroxide → HCID 21919288, compound

HRID 1244269Notes

Reaction equation

HRID 1244269 reaction equation
[OH-].[K+].COC(=O)[C:6]([C:16](=[O:18])[CH3:17])([CH2:13][CH2:14][CH3:15])[CH:7]([CH3:12])[C:8]([O:10]C)=[O:9]>CO.O>[C:16]([CH:6]([CH2:13][CH2:14][CH3:15])[CH:7]([CH3:12])[C:8]([OH:10])=[O:9])(=[O:18])[CH3:17]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 57551073HCID 57551073, compound

Product 1

HCID 21919288HCID 21919288, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

KOH (6.9 g, 123 mmol) is added to a solution of 2-acetyl-3-methyl-2-propyl-succinic acid dimethyl ester (5.0 g, 20.5 mmol) in MeOH (25 ml) and water (25 ml). The mixture is refluxed overnight and excess MeOH is evaporated. The residue is acidified by concentrated HCl to pH=2 and is refluxed (oil bath 105° C.) overnight. The mixture is extracted with EtOAc (4×75 ml) and the combined extracts are extracted with 2N aqueous NaOH (4×50 ml). The NaOH solution is then cooled to 0° C. and acidified with concentrated HCl. The mixture is extracted with EtOAc (4×75 ml) and the combined extracts are washed with brine (100 ml), dried (Na2SO4) and evaporated in vacuo, providing 3-acetyl-2-methyl-hexanoic acid as a yellow oil.

Workup

  1. temperatureThe mixture is refluxed overnight
  2. customexcess MeOH is evaporated
  3. extractionThe mixture is extracted with EtOAc (4×75 ml)
  4. extractionthe combined extracts are extracted with 2N aqueous NaOH (4×50 ml)
  5. temperatureThe NaOH solution is then cooled to 0° C.
  6. extractionThe mixture is extracted with EtOAc (4×75 ml)
  7. washthe combined extracts are washed with brine (100 ml)
  8. dry with materialdried (Na2SO4)
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-857f9d132bb74eaab9fb4693c0c5d0bc
Source dataset
uspto-grants-2006_10
Patent number
US07122546B2

Reaction notes

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