Sulfuric Acid → isopropyl (2R, 3R)-2-methyl-3-hydroxybutanoate

HRID 1900311Notes

Reaction equation

HRID 1900311 reaction equation
Cl[C:2](Cl)(Cl)[C@H:3]1[O:8][C:7](=[O:9])[C@H:6]([CH3:10])[C@@H:5]([CH3:11])[O:4]1.S(=O)(=O)(O)O.[CH3:19]C(O)C>O>[CH3:10][C@H:6]([C@H:5]([OH:4])[CH3:11])[C:7]([O:8][CH:3]([CH3:19])[CH3:2])=[O:9]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 53900667HCID 53900667, compound

Product 1

HCID 54130151isopropyl (2R, 3R)-2-methyl-3-hydroxybutanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1.0 g of (2R, 5R, 6R)-2-trichloromethyl-5,6-dimethyl-1,3-dioxan-4-one obtained by procedures similar to (1)-(4) of Example 1 were added 0.1 ml of concentrated sulfuric acid and 10 ml of 2-propanol and stirred at room temperature for one hour, and 20 ml of water was added to effect ether extraction. After drying the ether phase over anhydrous sodium sulfate, the ether was distilled off and the residue was subjected to distillation to give 0.4 g of isopropyl (2R, 3R)-2-methyl-3-hydroxybutanoate. The NMR chart is shown in FIG. 6. ##STR31##

Workup

  1. extractionether extraction
  2. dry with materialAfter drying the ether phase over anhydrous sodium sulfate
  3. distillationthe ether was distilled off
  4. distillationthe residue was subjected to distillation

Sources & evidence

ORD record
ord-f8e5d9e2231e4174a7b88f79ed2a9cc9
Source dataset
uspto-grants-1996_11
Patent number
US05574182

Reaction notes

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