Ethyl 2-methylacetoacetate → Ethyl 3-hydroxy-2-methylbutyrate

HRID 841101Notes

Reaction equation

HRID 841101 reaction equation
C(O)[C@H]1O[C@H](O[C@]2(CO)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O.[CH3:24][CH:25]([C:31]([CH3:33])=[O:32])[C:26]([O:28][CH2:29][CH3:30])=[O:27]>O>[OH:32][CH:31]([CH3:33])[CH:25]([CH3:24])[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

4

Reactant 2

HCID 701Ethyl 2-methylacetoacetateHCID 5988Sucrose2×

Product 1

HCID 656467Ethyl 3-hydroxy-2-methylbutyrateYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 6 L Erlenmeyer flask containing Baker's yeast (100 g) and sucrose (150 g) was added tap water (1000 mL) and the reaction mixture was mechanically stirred at room temperature for 0.5 h. Ethyl 2-methylacetoacetate (10 g, 0.0694 mol) was added to the reaction mixture and stirring continued for 24 h. Sucrose (50 g) was added and stirring continued for another 24 h. Hyflo super cel (50 g) was added to the reaction mixture and filtered through a sintered glass funnel. The aqueous solution was then extracted with ether (1.5 L), dried over sodium sulfate, and filtered. The solvent ether was removed via simple distillation to obtain ethyl 3-hydroxy-2-methylbutyrate (10 g, 100%) as a mixture of two isomers: 1H NMR (CDCl3) δ 1.18-1.30 (18H, m), 2.47-2.52 (2H, m), 3.85-3.91 (1H, m), 4.05-4.10 (1H, m), 4.13-4.21 (4H, m).

Workup

  1. stirringstirring
  2. waitcontinued for 24 h
  3. stirringstirring
  4. waitcontinued for another 24 h
  5. additionHyflo super cel (50 g) was added to the reaction mixture
  6. filtrationfiltered through a sintered glass funnel
  7. extractionThe aqueous solution was then extracted with ether (1.5 L)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customThe solvent ether was removed via simple distillation

Sources & evidence

ORD record
ord-e1f2acaa6d464f03963fdd9e644693c6
Source dataset
uspto-grants-2002_04
Patent number
US06369241B1

Reaction notes

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