3,5-Dichlorobenzaldehyde → HCID 67330016, compound

Participants

Reaction Conditions

Reaction Steps

The 2,2-Diethoxy-ethylamine (1852.5 g; 1.00 equiv; 13.63 moles), 3,5-dichloro-benzaldehyde (2453 g; 1.00 equiv; 13.60 moles), and Toluene (12 L) is charged to a 22 L flask equipped with a Dean Stark trap, condenser, nitrogen inlet, overhead stirring, and thermocouple. The light yellow reaction is warmed to reflux. Solvent begins distilling at 88° C. A total of ˜650 mL distillate (˜240 mL of water) is collected. The temperature is increased to 114° C. during the distillation. NMR after 2 hr at reflux shows the product. The heat is shut off after 2.5 hr. The solution is gravity filtered into a carboy through fluted filter paper to remove a few particulates (including a small section of glass tubing, which is most likely from the 3,5-dichloro-benzaldehyde). The filtered solution is concentrated using Buchi flask with the water bath set at 45° C. Once the solvent stops coming over, the temperature is increased to 70° C. with full vacuum and held for ˜1.5 hr to remove any residual toluene. The weight of (3,5-Dichloro-benzylidene)-(2,2-diethoxy-ethyl)-amine is 4059.3 g (102.9% of theory). Mass Spectrum (LCMS) m/z=291.2) (M+H+)

Provenance & Evidence