2,3-DIHYDROXY-4-METHOXYBENZALDEHYDE

To a stirredsolution of 2, 3, 4-trimethoxybenzaldehyde, 13 (0.80 g, 4.07 mmol) in CH2Cl2 (20 mL) was added 1 M BCl3(8.15 mL) dropwise at 0 C under nitrogen atmosphere. The mixture was stirred for 48 h at this temperature. Aftercompletion of the reaction, water (20 mL) was added. Themixture was then extracted with CH2Cl2 (3 × 70 mL), thecombined organic layer was washed with brine(2 × 50 mL), dried over anhydrous Na2SO4, filtered and thefiltrate was concentrated in vacuo. The crude residue was purifiedby column chromatography (EtOAc/hexane = 1/2) toyield the compound 17 (0.68 g, 99percent) as white solid. Rf = 0.14(EtOAc/hexane = 1/2); mp 93–95 C; 1H NMR (300 MHz, CDCl3) δ 11.12 (1H, s), 9.76 (1H, s), 7.22 (1H, d, J = 8.7 Hz), 6.63 (1H, d, J = 8.7 Hz), 5.46 (1H, s), 4.01(3H, s); 13C NMR (75 MHz, CDCl3) δ 195.0, 152.8, 148.9, 132.9, 126.0, 116.0, 103.5, 54.4.2, 3, 4-trimethoxybenzaldehyde (Compound 13) (0.80 g, 4.07 mmol) was reacted withTo a stirred solution of CH2Cl2 (20 mL) was added 1M BCl3 (8.15 mL) under a nitrogen atmosphere, at 0 ° C it was added dropwise. The reaction mixture was stirred at this temperature for 48 hours. After completion of the reaction, water (20 ml) was added. The reaction mixture was extracted with CH2Cl2 (3 x 70 mL)The organic layer was washed with brine (2 x 50 mL), dried over anhydrous Na2SO4, filtered and the filtrate was concentrated in vacuo.The crude compound was purified by column chromatography (EtOAc / hexane = 1/2) to obtain a white solid compound 17 (0.68 g, 99percent).A solution of 2, 3, 4-trimethoxybenzaldehyde (9.81 g, 50 mmol) was dissolved in CHBCl2, 3, 4-trimethoxybenzaldehyde, 1 (9.8 g, 50 mmol) was dissolved in anhydrous dichloromethane (150 ml) under argon at ambient temperature. A solution of 2, 3, 4-trimethoxybenzaldehyde 8 (5 mmol) in dry DCM (15 mL) was stirred at ambient temperature for 10 min, then 1 equivalent of BCl2, 3, 4-methoxybenzaldehyde (10.00mmol, 1962mg) was dissolved in 30mL anhydrous dichloromethane, stirred for 10 minutes at room temperature. Add 5mLBCl3 (1Minhexane) solution, after 2 hours, and then added 5mLBCl3 (1M in hexane) solution of , at room temperature for 24 hours. after the reaction is stopped by adding 5mL saturated aqueous sodium bicarbonate, the aqueous layer was adjusted with concentrated hydrochloric acid and PH = 1, the methylene chloride layer was separated. The aqueous layer was extracted with ethyl acetate, the combined organic phases were washed with saturated brine, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to give the crude product. By column chromatography eluting with petroleum ether condition; ethyl acetate = 1: 1 to give a yellow solid 1d 1227.9mg, yield 76.0percent, m.p. 107.4-108.8.2, 3-Dihydroxy-4methoxy-benzaldehyde (6b) 29. 2-Hydroxy-3-4-dimethoxybenzaldehyde (29) and 2, 3-Dihydroxy-4-methoxybenzaldehyde (29'); 2, 3, 4-Trimethoxybenzaldehyde (5.00 g, 25.5 mmol) was dissolved in dry CH

Molecular Weight:168.15
XLogP3:1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:168.04225873
Monoisotopic Mass:168.04225873
Topological Polar Surface Area:66.8
Heavy Atom Count:12
Complexity:159
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes