2,6-Dihydroxybenzaldehyde

2,6-dihydroxybenzaldehyde is a dihydroxybenzaldehyde.

Weigh AlCl3 (82.9g, 600mmol) in a 1L round bottom flask was added 500mL of methylene chloride was dissolved, stirred at room temperature. Weigh 2, 6-dimethoxybenzaldehyde (19.92g, 120mmol) dissolved in 200ml of dichloromethane was slowly added dropwise to the round bottom flask (dropping IH), after the addition was complete stirring was continued for 12h, after completion followed by TLC until the reaction was added dilute hydrochloric acid (2mol / L, 600mL) quenched organic phase was separated, the aqueous phase was extracted with ethyl acetate, the organic phases combined, dried over anhydrous sodium sulfate, filtered and spin dry the solvent, column chromatography (PE: EA = 9: 1), to give 12.5g of yellow solid, yield 78.3percent.Into a 3000-mL three neck round-bottom flask, was placed a solution of AlClInto a 3000-mL three neck round-bottom flask, was placed a solution of AlClTo a DCM solution (61.5 m L) of 2, 6-dimethoxybenzaldehyde (2.66 g, 16.0 mmol) was added boron tribromide (9.1 mL, 95 mmol) at 0 °C and the color of the mixture changed from colorless to red. After stirring for 1h at 0 °C, the solution was stirred for 20 h at room temperature. After the solution was poured onto ice and filtrated with suction, the organic phase was separated and the aqueous layer was extracted with DCM three times. The combined extracts were washed with brine and dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the residue was purified by column chromatography on silica gel (hexane/ethyl acetate 1:1) to give 2, 6-dihydroxybenzaldehyde (0.834 g, 38percent) as a yellow solid. To a DCM/pyridine solution (68 mL, 7:3) of 2, 6-dihydroxybenzaldehyde (0.556g, 4.02 mmol) was slowly added triflic anhydride (1.63 mL, 9.69 mmol) at 0 °C. The reaction mixture was warmed to room temperature and stirred for 3 h. After an aqueous hydrochloric acid (2 mol/L) was added, organic materials were extracted with ethyl acetate three times. The combined extracts were washed with brine and dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the residue was purified by column chromatography on silica gel (hexane/ethyl acetate 1:1) to give 2, 6-bis(trifluoromethanesulfonyloxy)benzaldehyde (1.37 g, 85percent) as a yellow solid.

Molecular Weight:138.12
XLogP3:1.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:138.031694049
Monoisotopic Mass:138.031694049
Topological Polar Surface Area:57.5
Heavy Atom Count:10
Complexity:114
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes