Hydrochloric Acid → Methyl 3-hydroxypivalate

HRID 1417810Notes

Reaction equation

HRID 1417810 reaction equation
[CH3:1][C:2]([CH3:8])([CH2:6][OH:7])[C:3]([OH:5])=[O:4].Cl.[CH3:10]O>>[CH3:1][C:2]([CH3:8])([CH2:6][OH:7])[C:3]([O:5][CH3:10])=[O:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 785483-Hydroxy-2,2-dimethylpropionic acid

Product 1

HCID 84152Methyl 3-hydroxypivalate

Procedure

A mixture of 2,2-dimethyl-3-hydroxypropionic acid (CXXXII, 11.54 g, 97.7 mmol), methanol (150 ml) and methanol (25 ml) saturated with hydrochloric acid gas is stirred overnight at 20°-25°. The mixture is then concentrated under reduced pressure, ether is added, and again the mixture is concentrated. The residue is dissolved in ether and poured cautiously into a small amount of saturated sodium bicarbonate. The phases are separated and the aqueous phase is washed several times with ether. The combined organic phases are backwashed with saline, dried over magnesium sulfate, and concentrated under reduced pressure to give methyl 2,2-dimethyl-3-hydroxypropionate (CXXXII), NMR (CDCl3) 1.20, 2.48, 3.56 and 3.71 δ.

Workup

  1. concentrationThe mixture is then concentrated under reduced pressure, ether
  2. additionis added
  3. concentrationagain the mixture is concentrated
  4. dissolutionThe residue is dissolved in ether
  5. additionpoured cautiously into a small amount of saturated sodium bicarbonate
  6. customThe phases are separated
  7. washthe aqueous phase is washed several times with ether
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b9622ad365b64f119fd54971b4ef0773
Source dataset
uspto-grants-1999_03
Patent number
US05877317

Reaction notes

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