2,3,4-Trimethoxybenzaldehyde

white to light yellow crystals or cryst. powder

General procedure: The O-methylation was performed by reaction of aldehydes 1a–7a with 4 equiv. of CH3I and 3 equiv.of K2CO3 to protect each hydroxyl group in acetone with heating at 80 °C for 12 h in Schlenk flask [20].Compounds were purified by column chromatography (cyclohexane/EtOAc, 9:1). Yields were 8a, 9a = 90percent; 10a, 11a = 92percent and 12a = 89percent.To a mixture of benzyl alcohol (0.5 mL, 4.64 mmol) and 15percent aqueous hydrogen peroxide(1.1 mL, 4.85 mmol), the catalyst [CuNi(-OAc)(-OH)(-OH2)(bpy)2](BF4)2 (8 mg, 0.01 mmol)was added and stirred at 70 °C for 5 h. The organic and aqueous phase were separated by aseparating funnel and then puried by column chromatography to aord benzaldehyde.The identity of the benzaldehyde was ascertained by comparison with authentic sampleusing IR, 1H NMR, and 13C NMR.General procedure: Benzyl alcohol (0.05g, 0.5mmol), was added to a mixture of 15percent HGeneral procedure: In a round-bottomed flask equipped with a stirring bar and rubber septum was placed a 1 M solution of SnCl4 in anhydrous CH2Cl2 (1 mL, 1 mmol). To this solution was added PhSCF2H (1; 240.2 mg, 1.5 mmol) in anhydrous CH2Cl2 (1.5 mL), followed by a solution of an aromatic compound (0.5 mmol) in anhydrous CH2Cl2 (1 mL). The reaction was allowed to proceed for 2 h before it was quenched with a solution of IBX (140 mg, 0.5 mmol) in DMSO/H2O (4 mL; 3:1 v:v). After 2 h of stirring at rt, the reaction mixture was quenched by addition of a saturated aqueous solution of sodium thiosulfate (10 mL), then basified with a saturated aqueous solution of sodium hydrogen carbonate (10 mL), followed by stirring and extraction with CH2Cl2 (3 × 10 mL). The combined organic layers were washed with water (3 × 10 mL) and brine (10 mL), dried (anhydrous MgSO4), filtered and concentrated (aspirator). The residue was purified by PTLC, radial chromatography or column chromatography to furnish analytically pure product.With a thermometer, Stirring and heating sets of three bottles, 123 g of the above intermediate 1, 2, 3-trimethoxybenzene was added, DMF 123 g, Dropping 246 g of phosphorus oxychloride, Dropping the end of heating to 70-80 ° C insulation 10 hours, Cooling The reaction solution was poured into 500 g of ice water for hydrolysis, 300 ml of ethyl acetate was extracted three times, Ethyl acetate was recovered under reduced pressure, The distillate was collected by distillation under reduced pressure, Cooling to obtain 115 g of white crystals, The product purity was 99.5percent and the total yield was 74percent by high performance gas chromatography.(1) The organic layer containing the intermediate (III) obtained above was placed in a 500 ml reaction flask, anhydrous magnesium chloride (13.5 g, 0.23 mol) was added, 35.4 g of paraformaldehyde was added in batches, and the dropwise addition was started. (38.6g, 0.28mol) potassium carbonate, after completion of the addition, heated to reflux, the reaction for 5 hours, the reaction solution was cooled to room temperature after the reaction was completed, then the reaction solution was slowly added dropwise to the amount of water, stirring was maintained for 30 minutes, static The layers are separated, the organic layer is collected, the organic layer is depressurized and the solvent is removed, and the fraction is collected by distillation under reduced pressure. The fraction is cooled and becomes white crystal (I) 24.4 g. The total yield is 82.9percent. Purity (HPLC area normalization method) 99.6percent.

2,3,4-Trimethoxybenzaldehyde is a trimethoxylated aromatic aldehyde. 2,3,4-Trimethoxybenzaldehyde is an Impurity of the anti-anginal drug Trimetazidine (T795610). Used as pharmaceutical intermediate

Molecular Weight:196.20
XLogP3:1.3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:196.07355886
Monoisotopic Mass:196.07355886
Topological Polar Surface Area:44.8
Heavy Atom Count:14
Complexity:183
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes