3-CHLORO-2-METHOXYBENZALDEHYDE

Manganese dioxide (16 g, 184 mmol) was added to a solution of the product of preparation 58 (5.68 g, 33 mmol) in dichloromethane (300 mL) and the mixture was heated for 45° C. for 2.5 hours and at room temperature for 18 hours. The mixture was then filtered through Arbocel.(R)., washing through with dichloromethane, and the filtrate was concentrated in vacuo to afford the title compound as a yellow oil in 92percent yield, 5.2 g. meta-Chloroperbenzoic acid (50-55%, 1.34 g, 40.9 mmol) was added to a solution of the product of preparation 61, (5.2 g, 30.5 mmol) in dichloromethane (120 mL) and the mixture was stirred at room temperature for 18 hours. The reaction mixture was then diluted with dichloromethane and washed with sodium sulphite, sodium hydrogen carbonate solution and evaporated under reduced pressure. The residue was dissolved in methanol (120 mL), triethylamine (0.5 mL) was added, and the mixture was stirred for 18 hours at room temperature. The mixture was then concentrated in vacuo and the residue was dissolved in 1M sodium hydroxide solution and washed with diethyl ether (×2). The aqueous phase was acidified to pH1 with concentrated hydrochloric acid and extracted with diethyl ether (×2). The combined organic extracts were dried over sodium sulfate and concentrated in vacuo to afford the title compound as a brown oil in 62% yield, 3 g. 1H NMR (CDCl3, 400 MHz) delta: 3.98(s, 3H), 6.89-6.99(m, 3H).

Molecular Weight:170.59
XLogP3:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:170.0134572
Monoisotopic Mass:170.0134572
Topological Polar Surface Area:26.3
Heavy Atom Count:11
Complexity:138
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes