Malonic Acid → HCID 12137093, compound

Temperature

80 °C

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).

1. customThe reaction was then quenched with water (50 mL)
2. custompartitioned with EtOAc (50 mL)
3. customthe layers separated
4. extractionThe aqueous layer was re-extracted with EtOAc (50 mL)
5. washthe combined organic layer washed with brine (80 mL)
6. concentrationconcentrated under vacuum
7. customto give a bright yellow solid
8. customPurification by SPE (silica, 20 g cartridge)
9. washeluting with cyclohexane

ORD record

ord-e6e18baa93bb42139a649c30c26d0bb8

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07338960B2