2-CHLORO-3-METHOXYPHENOL

3-Chloroperoxybenzoic acid (760mg, 4.396mmol) was added portionwise to a solution of 2- Chloro-3-Methoxybenzaldehyde (500mg, 2.931 mmol) in dichloromethane (12ml) and the mixture was stirred for 3 hours at room temperature. Further 3-chloroperoxybenzoic acid (760mg, 4.396mmol) was added and mixture allowed to stir for 18hrs. The solution was diluted with 12ml dichloromethane and washed with saturated sodium sulphite solution (15ml) and saturated sodium hydrogen carbonate solution (15ml). The organic layer was dried over sodium sulphate and concentrated in vacuo to a yellow gum. The residue was dissolved in methanol (12ml), triethylamine (0.05ml) was added and the mixture stirred for 18 hours at room temperature. The solution was concentrated in vacuo, dissolved in diethyl ether (20ml) and extracted with 1N sodium hydroxide (20ml). The aqueous layer was acidified to pH1 by dropwise addition of 2N hydrochloric acid and extracted with diethyl ether (2x25ml). These combined organic layers were dried over sodium sulphate and concentrated in vacuo to afford the title compound as a brown gum in 70percent yield, 325mg. To a solution of 2-Chloro-3-Methoxybenzaldehyde 2 (2 g, 11.7 mmol) in DCM (50ml) was added 3-Chloroperoxybenzoic acid (3 g, 17.Smmol) .The mixture was stirred for 12hours at 40°C. Filtered, the residue was contracted to a soled. The soled was desalted in 18mL of MeOH, then 5 mL of 10percent NaOH was added with cooling. After stirring for 45 mm at10°C, the mixture was condition at 30°Con a rotary evaporator to remove the MeOH, then 22mLof 5percent NaOH, was added and the solution was added with Conc HC1 with cooling, then extracted (3x20) with EA, wished with H20, 5percent NaHCO3, dried over Na2SO4 and concentrated in vacuo to afford the title compound (1.2 g, 66.6percent). ‘HNMR (400 MHz, CDC13): ö 7.14-7.10 (m, 1H), 6.67 (d, J 8.4 Hz, 1H), 6.51(d, J= 8.4 Hz, 1H), 5.62 (s, 1H), 3.89 (s, 3H).A) 2-chloro-3-methoxyphenol To an aqueous solution (100 mL) of potassium hydroxide (11.0 g) was added 2-chlorobenzene-l, 3-diol (22.8 g) . Then, dimethyl sulfate (19.9 g) was slowly added to the reaction mixture while keeping the reaction mixture at 10°C to 20°C, and the mixture was stirred at 100°C for 2 days. The reaction mixture was acidified with 2N hydrochloric acid, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (18.0 g) . 1R NMR (400 MHz, DMSO-d

Molecular Weight:158.58
XLogP3:2.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:158.0134572
Monoisotopic Mass:158.0134572
Topological Polar Surface Area:29.5
Heavy Atom Count:10
Complexity:108
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes