Benzyl Chloride → HCID 885478, compound

To a stirring solution of 3-chloro-4-hydroxy-5-methoxybenzaldehyde (599 mg, 3.21 mmol) in DMF (5 mL) under nitrogen was added Cs2CO3 (1.10 g, 3.38 mmol) followed by benzyl chloride (0.40 mL, 3.48 mmol) and the mixture heated at reflux for 1 h. After allowing the mixture to cool to ambient temperature the reaction was quenched by the addition of aqueous NaOH (2N, 30 mL) and the mixture concentrated under vacuum. The residue was then partitioned between NaOH (2N, 30 mL) and EtOAc (50 mL) and the layers separated. The aqueous layer was then re-extracted with EtOAc (50 mL), the layers separated and the combined organic layer washed with brine and then concentrated under vacuum. Purification by SPE (silica, 20 g cartridge) eluting with cyclohexane:EtOAc (gradient 50:1 to 10:1) afforded the title compound (632 mg).

1. temperaturethe mixture heated
2. temperatureat reflux for 1 h
3. customwas quenched by the addition of aqueous NaOH (2N, 30 mL)
4. concentrationthe mixture concentrated under vacuum
5. customThe residue was then partitioned between NaOH (2N, 30 mL) and EtOAc (50 mL)
6. customthe layers separated
7. extractionThe aqueous layer was then re-extracted with EtOAc (50 mL)
8. customthe layers separated
9. washthe combined organic layer washed with brine
10. concentrationconcentrated under vacuum
11. customPurification by SPE (silica, 20 g cartridge)
12. washeluting with cyclohexane

ORD record

ord-64e4b9ee417245d7a5e9fe4eb3c1ad6c

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07338960B2