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

HRID 35804Notes

Reaction equation

HRID 35804 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 18654774HCID 18654774, compound

Product 1

HCID 56973779isopropyl (2S, 3R)-2-methyl-3-hydroxybutanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1.0 g of (2R, 5S, 6R)-2-trichloromethyl-5,6-dimethyl-1,3-dioxan-4-one obtained by procedure similar to Example 1-(4) were added 0.1 ml of concentrated sulfuric acid and 10 ml of 2-propanol, stirred at room temperature for one hour, and 20 ml of water was added followed by ether extraction. The ether phase was dried over anhydrous sodium sulfate and ether was distilled off, and then the residue was subjected to distillation to obtain 0.4 g of isopropyl (2S, 3R)-2-methyl-3-hydroxybutanoate. ##STR41##

Workup

  1. extractionfollowed by ether extraction
  2. dry with materialThe ether phase was dried over anhydrous sodium sulfate and ether
  3. distillationwas distilled off
  4. distillationthe residue was subjected to distillation

Sources & evidence

ORD record
ord-200ed0ecda1945e8b1b680337cb3c45e
Source dataset
uspto-grants-1995_05
Patent number
US05411877

Reaction notes

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