Malonic Acid → HCID 12137093, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 4-hydroxy-2-methoxybenzaldehyde (1.02 g, 6.70 mmol) and malonic acid (728 mg, 7.00 mmol) in pyridine (9.2 mL) at ambient temperature under nitrogen was added piperidine (0.20 mL, 2.02 mmol) drop-wise. The mixture was then heated to 80° C. over 20 mins and then stirred at this temperature for 2 h. The reaction was then quenched with water (50 mL), acidified to pH 1 with concentrated HCl and then partitioned with EtOAc (50 mL) and the layers separated. The aqueous layer was re-extracted with EtOAc (50 mL) and the combined organic layer washed with brine (80 mL) and then concentrated under vacuum to give a bright yellow solid. Purification by SPE (silica, 20 g cartridge) eluting with cyclohexane:EtOAc (gradient 25:1 to 0:1) afforded the title compound (674 mg).

Provenance & Evidence