ChemicalBook CAS DataBase List 2,4,5-Trimethoxybenzaldehyde

2,4,5-Trimethoxybenzaldehyde synthesis

7synthesis methods

Product Name:2,4,5-Trimethoxybenzaldehyde
CAS Number:4460-86-0
Molecular formula:C10H12O4
Molecular Weight:196.2

1535-67-7 Synthesis

1535-67-7
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$30.00/250mg

135-77-3
335 suppliers
$5.00/5g

4460-86-0
441 suppliers
$5.00/100mg

Yield:4460-86-0 98%

Reaction Conditions:

Stage #1:difluoromethyl phenyl sulfide;1,2,4-trimethoxy-benzene with tin(IV) chloride in dichloromethane at 20; for 2 h;Inert atmosphere;
Stage #2: with 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in dichloromethane;water;dimethyl sulfoxide at 20; for 2 h;

Steps:

Aldehydes 4 and 8; General Procedure
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.

References:

Betterley, Nolan M.;Kongsriprapan, Sopanat;Chaturonrutsamee, Suppisak;Deelertpaiboon, Pramchai;Surawatanawong, Panida;Pohmakotr, Manat;Soorukram, Darunee;Reutrakul, Vichai;Kuhakarn, Chutima [Synthesis,2018,vol. 50,# 10,p. 2033 - 2040]

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