Methanol → Methyl 2-ethyl-2-hydroxybutanoate

HRID 1672290Notes

Reaction equation

HRID 1672290 reaction equation
[CH2:1]([C:3]([OH:9])([CH2:7][CH3:8])[C:4]([OH:6])=[O:5])[CH3:2].S(=O)(=O)(O)O.[CH3:15]O>>[CH2:1]([C:3]([OH:9])([CH2:7][CH3:8])[C:4]([O:6][CH3:15])=[O:5])[CH3:2]

Participants

4

Procedure

To a solution of 2-ethyl-2-hydroxybutyric acid (5.00 g) in methanol (35 mL) was added conc. sulfuric acid (0.25 mL), and the mixture was refluxed at room temperature for 18 hours and then refluxed under heating for 18 hours. After cooling, the reaction mixture was concentrated in vacuo, and the resultant residue was diluted with diethylether. The mixture was washed successively with an aqueous saturated sodium hydrogencarbonate solution and brine, dried over sodium sulfate and concentrated in vacuo. The residue was distilled to give methyl 2-ethyl-2-hydroxybutyrate (3.70 g) as a colorless oil,

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 18 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated in vacuo
  5. additionthe resultant residue was diluted with diethylether
  6. washThe mixture was washed successively with an aqueous saturated sodium hydrogencarbonate solution and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. distillationThe residue was distilled

Sources & evidence

ORD record
ord-0a8e1917ec2d4532888d0b26a3396803
Source dataset
uspto-grants-2011_08
Patent number
US07998956B2

Reaction notes

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