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 1N HCl, 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 1N HCl, 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-978831c3f1d84dec8a1e9d05455b6240

Source dataset

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06780872B2