Potassium Sodium Tartrate → 3-Iodo-4-methylbenzaldehyde

Participants

Reaction Conditions

Reaction Steps

3-Iodo-4-methylbenzoic 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 was dissolved in THF (200 mL) and treated with a 1M solution of lithium tri-tert-butoxyaluminohydride in THF (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 and brine, dried over Na2SO4, and concentrated. The resulting residue was purified by flash chromatography using hexanes:ethyl acetate (4:1) as the eluent to provide the title compound as a white solid (300 mg, 18%).

Provenance & Evidence