Potassium Sodium Tartrate → 3-Iodo-4-methylbenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a slurry of 3-iodo-4-methylbenzoic acid (1.0 g,3.96 mmol) in 200m1 of dry CH2Cl2-THF (1:1) was added oxalyl chloride (1 ml, 11.9 mmol) and several drops of DMF. This mixture was heated at 65° C. for 30 min, cooled to room temperature, and concentrated to form light yellow solids. The solids were dissolved in 200ml of THF and cooled to -78° C.. A solution of lithium tri-tert-butoxyaluminohydride (4.1 ml, 4.1 mmol) was syringed into the reaction mixture. After 30 minutes at -78 ° C., a solution of saturated Rochelle′s salt was added to quench the reaction at -78 ° C.. The mixture was allowed to warm to ambient temperature and the layers separated. The organic layer was washed with IN HCl, sat NaHCO3 and brine, dried (Na2SO4), concentrated and the resulting residue was purified by flash chromatography using hexane/EtOAc (4:1) as eluent to yield the title compound as a white solid (300 mg, 18%).

Provenance & Evidence