Benzaldehyde,4-chloro-3-hydroxy-

Intermediate 28a and 28b 2-chloro-5-hydroxybenzaldehyde (28a) and 4-chloro-3- hydroxybenzaldehyde ( To a solution of 3-hydroxybenzaldehyde (1 g, 10 mmol) in acetonitrile (50 mL) was added p- toluenesulfonic acid (3.4 g, 20 mmol) portionwise. The mixture was stirred at room temperature for 5 min, and NCS (1.33 g, 10 mmol) was added and the resulting mixture was stirred at room temperature for 2 h. The mixture was quenched with aqueous sodium thiosulfate, and diluted with ethyl acetate and brine. The organic layer was separated, dried, and concentrated to give the crude products which were purified by silica gel chromatography eluting with petroleum ether /ethyl acetate (10: 1 to 5: 1) to give 2-chloro-5-hydroxybenzaldehyde (340 mg, 21.7percent yield intermediate 28a) as yellow solid; 'H-NMR (CDC1To a solution of 3-hydroxybenzaldehyde (1 g, 10 mmol) in acetonitrile (50 mL) was added p-toluenesulfonic acid (3.4 g, 20 mmol) portionwise. General procedure: 5 mmol formyl substituted phenol and 10 mmolK2CO3 were mixed fully in 25 mL acetonitrile, then 10mmol ethyl 2-bromo-2-methylpropanoate was added. The mixture was refluxed forabout 6 h. When it cooled to room temperature, the mixture was suctionfiltered, and filter cake was washed by acetonitrile. Combined filtrate wasevaporated with vacuum distillation. Crude product was added 20 mL water, andextracted with ethyl acetate (20 mL × 3). The extracts were washed withsaturated NaCl solution, dried over by anhydrous Na2SO4, filtered and evaporated under reduced pressure. The residue purified by columnchromatography on silica gel (ethyl acetate / petroleum ether) to intermediate products.

Molecular Weight:156.56
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:155.9978071
Monoisotopic Mass:155.9978071
Topological Polar Surface Area:37.3
Heavy Atom Count:10
Complexity:127
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes