Example 106: Synthesis of methyl 2-(hydroxymethyl)acrylate
Trimethylphosphonoacetate (5.46 g, 30 mmol, 1.0 eq.) was dissolved in an appropriate amount of solvent at room temperature with rapid stirring. Subsequently, saturated K2CO3 aqueous solution (10 mL, 3.5 g, 117 mmol, 1.6 equiv) was added slowly. Next, paraformaldehyde (6.63 g, 48 mmol, 4.0 eq.) was added. After the addition was completed, the reaction mixture continued to be stirred for 2 hours. After completion of the reaction, the mixture was extracted with dichloromethane (DCM). The organic layers were combined and concentrated to give the target product methyl 2-(hydroxymethyl)acrylate (1.5 g, 44% yield) as a yellow oil. The product was characterized by 1H NMR (400 MHz, CD3OD) with the following chemical shifts: δ 6.29 (s, 1H), 5.83 (s, 1H), 3.75 (s, 3H), 3.72 (s, 2H).
