Hydrochloric Acid → Methyl 3-hydroxypivalate

HRID 368829Notes

Reaction equation

HRID 368829 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 mi) 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-f7f930875e444762b6381c86a7f83b64
Source dataset
uspto-grants-2000_10
Patent number
US06133446

Reaction notes

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