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

HRID 35805Notes

Reaction equation

HRID 35805 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 57102388HCID 57102388, compound

Product 1

HCID 57291196isopropyl (2S, 3S)-2-methyl-3-hydroxybutanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1.0 g of (2S, 5S, 6S)-2-trichloromethyl-5,6-dimethyl-1,3-dioxan-4-one obtained by procedure similar to Example 1-(7) 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 the residue was subjected to distillation to give 0.4 g of isopropyl (2S, 3S)-2-methyl-3-hydroxybutanoate of the following formula. ##STR51##

Workup

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

Sources & evidence

ORD record
ord-185c52e8bb324c2f9801394e75d52aba
Source dataset
uspto-grants-1995_05
Patent number
US05411877

Reaction notes

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