O-Cresol → 3-Methylsalicylaldehyde

Participants

Reaction Conditions

Reaction Steps

o-Cresol 20.0 g (185 mmol) was dissolved in toluene 400 ml and thereto was added 2,6-lutidine 18.4 g (171 mmol). SnCl4 4.8 g (18 mmol) was added to the mixture and the mixture was stirred for 30 min. at 20° C. Thereto was added paraformaldehyde (purity: 95 weight %) 12.9 g (409 mmol) and the mixture was stirred at 80° C. for 5 hours to the conversion of 78%. And the reaction was kept for 10 hours at 100° C. to confirm the disappearance of the raw material, o-cresol. The reaction solution was cooled to room temperature, extracted with water-toluene in a separatory funnel and the organic layer was dried over anhydrous magnesium sulfate and dried in vacuo to give 2-hydroxy-3-methylbenzaldehyde 24.9 g (yield: 99%, selectivity: 99%).

Provenance & Evidence