2,4,6-Trimethoxybenzaldehyde

pink crystal power

2, 4, 6-Trimethoxy-benzaldehyde2, 4, 6-Trimethoxy-benzene (40gm, 0.22x10In a round bottom flask, POCl3 (7.3 ml, 80 mmol) was added to a mixture of 1, 3, 5-trimethoxybenzene (8.41 g, 50 mmol) in DMF (15 ml). The temperature of reaction mixture was kept below 30° C. by slowly adding POCl3. After addition of POCl3, the mixture was still stirred at room temperature for an addition 1 hour. The reaction mixture was added into a cold saturated NaHCO3 solution. The pH of the solution was adjusted to remain above 7. Precipitation of desired product occurred. The off-white product was filtered and rinsed with NaHCO3 aq., then with HCl aq. 0.5M and then with water. Off-white solid was collected and vacuum dried at room temperature to yield 14a (9.60 g, 48 mmol, 98percent).Dimethylformamide (9.0 mL, 8.4 g, 0.116 mol) was addedto trimethoxy-phloroglucinol (15.0 g, 0.089 mol) andcooled at 0 °C. Phosphorousoxychloride (9.1 mL, 15.0 g)was added dropwise to this cooling mixture slowly underanhydrous conditions. The mixture was then allowed to stand for 1 h at room temperature. The reaction was monitoredby TLC using 40percent ethyl acetate in Hexane as mobilephase. After completion the reaction mixture was pouredinto crushed-ice and basified with 8M KOH. The solidprecipitate obtained was filtered and dried at 80 °C (VasuBabu et al. 2013). Pale pink color powder with 91.6percent ofyield obtained with melting point 119–121 °C (Scheme 1).Using 1, 3, 5-trimethoxybenzene (I) as raw material, the reaction intermediate 2, 4, 6-trimethoxybenzaldehyde (IV) was prepared by Vilsmeier-Haauc acylation reaction.[0036]In a 250 ml three-neck flask equipped with a stirrer and placed in an ice bath, Add 8.76 g (0.12 mol) DMF, Then add 9.8g (0.064mol) P0C13 slowly to the three-necked flask.The Vi 1 smeier complex is formed after 0.5 h of reaction.Then 10.10g (0.06mol)1 , 3 , 5-trimethoxybenzene was gradually added to this complexation solution.Then, the ice bath was removed, the condenser was placed, the reaction flask was transferred to a 30°C water bath and the reaction was stirred for 3 h to form an intermediate. The intermediate reaction solution was poured into a beaker of 60 ml of ice water and stirred with a glass rod. After mixing, seal the membrane at the mouth of the beaker and place it in a refrigerator at 4 °C for cooling and crystallization. The following day's extraction gave 8.8 g of a beige-white powdery product with a yield of 74.68percent.100 g of the compound SM (phloroglucinol trimethylether) and 500 ml of DMF were mixed, Ice salt bath cooling to below 0 , Dropping 201 g (2.2 eq) of phosphorus oxychloride, controlling the temperature below 0 ° C, Canada completed, the following 0 insulation reaction 1h, TLC followed the completion of the reaction; the reaction solution poured into ice water, potassium carbonate solution adjusted to weakly alkaline (pH 8-10), crystallization overnight, filtered to obtain a white solid, dried to 101g product (Compound I) Hydrogen nuclear magnetic resonance (HNMR) spectrum shown in Figure 1.General 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. 2, 4, 6-Trimethoxybenzaldehyde (4b) White solid (97.12 mg, 99 percent) from EtOAc/hexanes; mp 118–120 °C; Rf = 0.23 (hexanes/EtOAc, 5:1). IR (KBr): 2976, 2949, 2880, 1664 (C=O), 1600, 1475, 1333, 1161, 1127, 1025 cm–1. 1H NMR (300 MHz, CDCl3): δ = 10.36 (s, 1 H), 6.09 (s, 2 H), 3.89 (s, 9H). 13C NMR (75 MHz, CDCl3): δ = 187.6 (CO), 166.2 (C), 164.1 (2 × C), 108.9 (C), 90.3 (2 × CH), 56.0 (2 × CH3), 55.5 (CH3). HRMS (ESI-TOF): m/z [M + Na]+ calcd for C10H12O4Na: 219.0633; found: 219.0627.General procedure: The appropriate benzene derivative (3.2–10.6 mmol) was dissolved in dry DCM (10–20 mL), purged with Ar, and cooled with an ice bath to 0 °C. Next, TiClGeneral procedure: Chloramine-T (0.5 equiv) was added to a solution of KGeneral procedure: n-BuLi (1.67 M solution in hexane, 1.3 mL, 2.2 mmol) was added dropwise into a solution of p-bromoanisole (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, DMF (0.22 mL, 2.2 mmol) was added to the mixture and the obtained mixture was stirred at rt. After 2 h at the same temperature, THF was removed. Then, MeOH (3 mL) was added to the residue and the mixture was stirred at room temperature. After 30 min, I

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:169
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes