Potassium Sodium Tartrate → 3-Iodo-4-methylbenzaldehyde

Temperature

65 °C

3-Iodo-4-methyl-benzoic acid (1.0 g, 3.96 mmol) in dry CH2Cl2:THF 1:1 (200 mL) was treated with oxalyl chloride (1 mL, 11.9 mmol) and several drops of DMF. The mixture was heated at 65° C. for 30 minutes, cooled to ambient temperature, and concentrated under reduced pressure to provide a light yellow solid. The obtained solid in THF (200 mL) was treated with LiAlH(OtBu)3 (4.1 mL, 4.1 mmol) via syringe at −78° C. After 30 minutes at −78° C., a saturated solution of Rochelle's salt was added and the mixture was allowed to warm to ambient temperature. The organic layer was washed in succession with 1 NHCl, saturated NaHCO3, brine, dried over Na2SO4, and the solvent removed under reduced pressure. The resulting residue was purified by flash chromatography using hexanes:EtOAc (4:1) as eluent to provide 3-iodo-4-methylbenzaldehyde as a white solid (300 mg, 18%).

1. temperaturecooled to ambient temperature
2. concentrationconcentrated under reduced pressure
3. customto provide a light yellow solid
4. temperatureto warm to ambient temperature
5. washThe organic layer was washed in succession with 1 NHCl, saturated NaHCO3, brine
6. dry with materialdried over Na2SO4
7. customthe solvent removed under reduced pressure
8. customThe resulting residue was purified by flash chromatography

ORD record

ord-8be7e6f840834857af7f0bcd7c59c9ca

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06538004B2