p-Toluenesulfonic acid → HCID 21886104, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromosalicylaldehyde (41.0 g, 0.200 mol), trimethyl orthoformate (205 ml, 1.83 mol) and dry p-toluenesulfonic acid (1.77 g, 0.010 mol) was refluxed for 24 h. After the reaction mixture was cooled to the RT, sodium bicarbonate (50 g) was carefully added, and the mixture was ultrasonicated for 5 min. The liquid was separated; the solid was washed with dry benzene (25 ml) and removed by filtration. Combined solutions were evaporated. The residue was triturated with dry hexane (30 ml) if necessary cooled to −18° C. Precipitate formed was collected by filtration, washed with dry hexane (20 ml). Slightly yellow crystals, 44.2 g (0.179 mol, 89%).

Provenance & Evidence