Methanol → [2-(2-Methoxyethoxy)ethyl]malonic acid

Participants

Reaction Steps

Sodium hydroxide (2.00 g, 50.00 mmol) in water (15 mL) was added to a stirred solution of diethyl[2-(2-methoxyethoxy)ethyl]malonate (Step 1) (2.35 g, 8.96 mmol). The reaction was kept at ambient temperature for 10 minutes before MeOH was removed in vacuo. The resulting solution was acidified to pH=1 by the addition of HCl (5 M). Diethyl ether was added and the two phases were separated. The aqueous phase was extracted three times with diethyl ether. The organic extracts were combined, dried over MgSO4 and concentrated in vacuo to give the title compound as a colourless oil (1.81 g), 1H NMR (300 MHz, CDCl3) δ 7.16 (br s, 2H), 3.58 (m, 7H), 3.40 (s, 3H), 2.23 (m, 2H).

Provenance & Evidence