3,5-Dimethylphenol → HCID 591070, compound

Participants

Reaction Conditions

Reaction Steps

3,5-Dimethylphenol (40.0 g; 330 mmole) was dissolved in dichloromethane (210 ml) and the solution was cooled to a temperature of 0° C. Titanium tetrachloride (105 g; 553 mmole) was added dropwise over a period of 5 minutes to the stirred solution and then the temperature of the solution was maintained at 0° C. for a period of 30 minutes while dichloromethyl methyl ether (31.6 g) was added dropwise. The solution was warmed to room temperature and stirred for a period of 30 minutes and then warmed to 35° C. and stirred for a further 15 minutes. The reaction mixture was poured onto ice (ca 300 g) and the aqueous mixture was extracted with dichloromethane. The organic phase was washed three times with water and the solvent was removed by evaporation under reduced pressure. The residue was steam distilled and the distillate was extracted with dichloromethane and the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give 2,4-dimethyl-6-hydroxybenzaldehyde (31.0 g; 63.0%) as a yellow solid mp <50° C. Proton magnetic resonance spectrum (CDC13 ; δ in ppm): 2.19 (3H, s); 2.42 (3H, s); 6.41-6.52 (2H, m); 10.05 (1H, s); 11.90 (1H, s).

Provenance & Evidence