Acetic Acid → 3,5-Dichloro-4-hydroxybenzaldehyde
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[OH:9].C1N2CN3CN(C2)CN1C3.S(=O)(=O)(O)O.[C:25](O)(=[O:27])C>>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([Cl:8])[C:3]=1[OH:9])[CH:25]=[O:27]Participants
5
Conditions
- Temperature
- 100 °C
Procedure
A 250 ml three neck round bottom flask fitted with reflux condenser, pot thermometer and mechanical stirrer, was charged with 10 g (0.061 mol) of 2,6-dichlorophenol, 40 ml glacial acetic acid and 3.44 g (0.024 mol) of hexamethylenetetramine. The reaction mass was heated at reflux for 3 hrs (a clear solution was obtained at 70° C.). The progress of reaction was checked by TLC. The mixture was allowed to cool at 100° C.; 30 ml of 10% sulphuric acid were slowly added and stirred at 100° C. for 20-30 min. The reaction mass was poured into 200 g crushed ice. The solid was filtered and washed well with 100 ml water and drying at 70° C. afforded 9.2 g (84%) of 3,5-dichloro-4-hydroxy-benzaldehyde. Melting point: 153-155° C. 1H NMR (400 MHz, CD3OD) δ 9.72 (s, 1H), δ 7.80 (s, 1H).