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

HRID 35806Notes

Reaction equation

HRID 35806 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 57270836isopropyl (2R, 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 produced by a 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 to effect ether extraction. The ether phase was dried over anhydrous sodium sulfate and ether was distilled off followed by distilling the residue to obtain 0.4 g of isopropyl (2R, 3S)-2-methyl-3-hydroxybutanoate of the following formula. ##STR61## (2) Repeating the procedure of Example 5-(1) except that 2-propanol was replaced with 2-butanol, 0.5 g of 1-methylpropyl (2R, 3S)-2-methyl-3-hydroxybutanoate of the following formula was obtained.

Workup

  1. extractionether extraction
  2. dry with materialThe ether phase was dried over anhydrous sodium sulfate and ether
  3. distillationwas distilled off
  4. distillationby distilling the residue

Sources & evidence

ORD record
ord-e524e68b961847e189e32cc1fcedfdbf
Source dataset
uspto-grants-1995_05
Patent number
US05411877

Reaction notes

Loading…