Isopropyl iodide → HCID 22930520, compound

A mixture of 2-iodo-propane (2.2 ml, 22 mmol), methyl 5-chloro-2-hydroxy-benzoate (2.0 g, 10.7 mmol), potassium carbonate (3.0 g, 10.9 mmol), and acetonitrile (40 ml) was heated under reflux for 3 hours. After cooling to room temperature, the mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was partitioned between ethyl acetate (100 ml) and saturated aqueous sodium chloride solution (100 ml). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with dichloromethane-hexane (1:3 followed by 1:2 followed by 1:1) to provide methyl 5-chloro-2-isopropoxy-benzoate (1.2 g, 49% yield).

1. temperaturewas heated
2. temperatureunder reflux for 3 hours
3. filtrationthe mixture was filtered
4. concentrationthe filtrate was concentrated under reduced pressure
5. customThe residue was partitioned between ethyl acetate (100 ml) and saturated aqueous sodium chloride solution (100 ml)
6. dry with materialThe organic layer was dried over sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by flash chromatography on silica gel eluting with dichloromethane-hexane (1:3 followed by 1:2 followed by 1:1)

ORD record

ord-b59bfcaf11d641bdbbad5030ac8f4ce6

Source dataset

uspto-grants-2007_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07291616B2