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

HRID 1900312Notes

Reaction equation

HRID 1900312 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 a 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-d14b9905c3054ec8bc05a0a7d8bf6852
Source dataset
uspto-grants-1996_11
Patent number
US05574182

Reaction notes

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