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 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).

Provenance & Evidence