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

HRID 1993685Notes

Reaction equation

HRID 1993685 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 through the week-end (ca. 70 h). 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 layers over MgSO4. Filter and concentrate under reduced pressure to yield 3-hydroxy-2-hydroxymethyl-2-methyl-propionic acid methyl ester. 1H NMR (CDCl3, 300 MHz): δ ppm 3.9 (d, 2H, J=11.1. Hz), 3.76 (s, 3H), 3.71 (d, 2H, J=1-1. 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 layers over MgSO4
  4. filtrationFilter
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-d94e20dddac4441182df02a89d0f33c8
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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