Hydrochloric Acid → (2R, 3S)-3-methoxy-2-methylbutyric acid

HRID 2253566Notes

Reaction equation

HRID 2253566 reaction equation
[CH3:1][O:2][C@@H:3]([CH3:11])[C@@H:4]([CH3:10])[C:5]([O:7]CC)=[O:6].Cl.O>O1CCOCC1>[CH3:1][O:2][C@@H:3]([CH3:11])[C@@H:4]([CH3:10])[C:5]([OH:7])=[O:6]

Participants

5

Conditions

Temperature
90 °C

Procedure

This methyl ether (2.55 g) was dissolved in dioxane (50 ml) and conc. hydrochloric acid (36 %, 10 ml) and water (50 ml) were added to the solution. The solution was heated at 90° C. for 5 hours. The reaction mixture was poured into water (100 ml) and the mixture was extracted 4 times with ethyl acetate. The combined extract was dehydrated, concentrated and distilled under reduced pressure (b.p. 105° C./1 mmHg) to obtain (2R, 3S)-3-methoxy-2-methylbutyric acid (1.49 g).

Workup

  1. extractionthe mixture was extracted 4 times with ethyl acetate
  2. extractionThe combined extract
  3. concentrationconcentrated
  4. distillationdistilled under reduced pressure (b.p. 105° C./1 mmHg)

Sources & evidence

ORD record
ord-cd6903b1cba84f92b95a3f4335cddf09
Source dataset
uspto-grants-1993_08
Patent number
US05232853

Reaction notes

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