3,5-DICHLORO-4-HYDROXYBENZALDEHYDE

General procedure: a mixture of substrate 1a(1 mmol), cobalt salt (n2, 6-Dichloro-4-hydroxymethylphenol (3.56 g, 18.4 mmol) was dissolved in dioxane, and DDQ (4.19 g, 18.4 mmol) was added. The reaction mixture was stirred at rt overnight. The solvents were removed under reduced pressure. The residue was diluted with CH2CI2, and the mixture was filtered. The filtrate was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Crystallization from EtOAc yielded the title compound (0.77g, 22percent). LC-MS: t2, 6-Dichloro-4-hydroxymethylphenol (3.56 g, 18.4 mmol) was dissolved in dioxane, and DDQ (4.19 g, 18.4 mmol) was added. The reaction mixture was stirred at rt overnight. The solvents were removed under reduced pressure. The residue was diluted with CH2, 6-Dichloro-4-hydroxymethylphenol (3.56 g, 18.4 mmol) was dissolved in dioxane, and DDQ (4.19 g, 18.4 mmol) was added. The reaction mixture was stirred at rt overnight. The solvents were removed under reduced pressure. The residue was diluted with CHaCk, and the mixture was filtered. The filtrate was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Crystallization from EtOAc yielded the title compound (0.77g, 22percent). LC-MS: t2, 6-Dichloro-4-hydroxymethylphenol (3.56 g, 18.4 mmol) was dissolved in dioxane, and DDQ (4.19 g, 18.4 mmol) was added. The reaction mixture was stirred at rt overnight. The solvents were removed under reduced pressure. The residue was diluted with CHCompound R53 (4.9 g, 40 mmol) was dissolved in 80 ml of dry chloroform, followed by argon gasProtected, heated to reflux, slowly added dropwise a solution of 20 ml of sulfonyl chloride (6.4 ml, 80 mmol) in chloroform, and then refluxed overnight. The reaction solution was spin-dried and purified on a silica gel column. Yield 4.2g (55percent).: Synthesis of 2, 6-dichlorobenzene-1 , 4-diol; 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 00°C; 30 ml of 10 percent 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 percent) of 3, 5-dichloro-4-hydroxy-benzaldehyde. Melting point: 153- 155°C. 1 H NMR (400 MHz, CD General procedure: Piperidine (8.7 muL, 0.088 mmol), 3, 5-difluoro-4-hydroxybenzaldehyde (69.5 mg, 0.44 mmol) and S3 (100.0 mg, 0.44 mmol) were dissolved in EtOH (2.0 mL). The mixture was heated to 80 oC for 16 h. The orange solid was filtered and washed with 1N HCl and Et2O to afford 3 (114.0 mg, 70percent, mixture of E/Z isomers).General procedure: A solution of the selected phenol (10 mmol) and hexamethylenetetramine (11 mmol, 1.550 g) in trifluoroacetic acid (10 mL) was stirred and heated at reflux overnight. After cooling to room temperature, the crude product mixture was evaporated under reduced pressure and the yellow residue obtained was poured into distilled water and crushed ice. The cream-colored solid that precipitated was filtered under reduced pressure, washed with distilled water and dried at room temperature under vacuum, yielding the desired compound as a white solid. See, e.g., (Scheme 1, Figure 2). Yield: 60percent, 940 mg;quaternary ammonium compounds, such asN-alkyl-N, N-dimethylbenzyl ammonium chloride and...cetylpyridinium chloridediguanidinepolybiguanide1, 2-dibromo-2, 4-dicyanobutane3, 5-dichloro4-hydroxybenzaldehydeethylene glycol hemiformaldichlorophen2, 2-dibromo-3-nitrilopropionic acid amide...Stage A Quaternary ammonium compounds such asN-alkyl-N, N-dimethylbenzylammonium chloride anddi-n-decyldimethylammonium chlorideCetylpyridinium chlorideDiguanidine1, 2-Dibromo-2, 4-dicyanobutane3, 5-Dichloro-4-hydroxybenzaldehydeEthylene glycol hemiformal

Molecular Weight:191.01
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:189.9588348
Monoisotopic Mass:189.9588348
Topological Polar Surface Area:37.3
Heavy Atom Count:11
Complexity:139
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes