Water → 2,3,4,5-Tetramethoxy-6-methylbenzaldehyde

Participants

Reaction Steps

According to the procedure by Ohkawa et al.,15 6 (0.690 g, 3.25 mmol) was dissolved in CH2Cl2 (2.0 mL) in a flame-dried 25 mL round bottom flask and cooled to 0° C. α,α-dichloromethyl methyl ether (0.85 ml, 9.6 mmol) was then added at 0° C., followed by TiCl4 (1 M in CH2Cl2, 9.0 ml, 9.0 mmol) at 0° C. The reaction was warmed slowly to room temperature and stirred for 6 hours under argon. The reaction was then poured into chilled water and stirred for 10 minutes. The reaction was diluted with EtOAc, washed with brine, dried over MgSO4, filtered, and condensed. The crude oil was then purified by flash chromatography (1:49 EtOAc:hexanes if made via p-cresol; 3:17 EtOAc:hexanes if made via Wolffe-Kishner reduction) to provide 7 (0.696 g, 2.90 mmol, 89%) as a yellow oil.

Provenance & Evidence