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

Participants

Reaction Steps

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)

Provenance & Evidence