Methanol → Propanoic acid, 3-hydroxy-2-(hydroxymethyl)-2-methyl-, methyl ester

HRID 729594Notes

Reaction equation

HRID 729594 reaction equation
OS(O)(=O)=O.[OH:6][CH2:7][C:8]([CH2:13][OH:14])([CH3:12])[C:9]([OH:11])=[O:10].[CH3:15]O>>[CH3:15][O:10][C:9](=[O:11])[C:8]([CH2:13][OH:14])([CH3:12])[CH2:7][OH:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 78501Dimethylolpropionic acid

Product 1

HCID 87346Propanoic acid, 3-hydroxy-2-(hydroxymethyl)-2-methyl-, methyl ester

Procedure

Add H2SO4 (4.5 g) to a suspension of 3-Hydroxy-2-hydroxymethyl-2-methyl-propionic acid (100 g) in MeOH (1 L, HPLC grade solvent) and stir at room temperature. for about 70 hours. Remove the solvent and partition the residue between EtOAc (1 L) and H2O (100 mL). Re-extract the aqueous layer with EtOAc, and dry the combined organic fractions over MgSO4. Filter and concentrate under reduced pressure. Crude mixture can be used without further purification. 1H NMR (CDCl3, 300 MHz): δ ppm 3.9 (d, 2H, J=11.1 Hz), 3.76 (s, 3H), 3.71 (d, 2H, J=11.1 Hz), 2.8 (bs, 2H), 1.1 (s, 3H)

Workup

  1. customRemove the solvent
  2. custompartition the residue between EtOAc (1 L) and H2O (100 mL)
  3. dry with materialRe-extract the aqueous layer with EtOAc, and dry the combined organic fractions over MgSO4
  4. filtrationFilter
  5. concentrationconcentrate under reduced pressure
  6. customCrude mixture can be used without further purification

Sources & evidence

ORD record
ord-ef38ae324b6d4c568ecf51230f26dc80
Source dataset
uspto-grants-2009_09
Patent number
US07582638B2

Reaction notes

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