Sulfuric Acid → 2-Hydroxy-5-trifluoromethylbenzaldehyde

Participants

Reaction Steps

To a mixture of 4.91 g of 4-(trifluoromethyl)phenol and 68 ml of trifluoroacetic acid was gradually added 4.67 g of hexamethylenetetramine at room temperature. This mixture was heated under reflux for 24 hours. The reaction mixture was cooled to room temperature, then 35 ml of water and 19 ml of 50% sulfuric acid were added to the reaction mixture, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was extracted three times with diethyl ether. The organic layers were combined and sequentially washed with 5 M hydrochloric acid and water. The organic layer was dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.7 g of 2-hydroxy-5-(trifluoromethyl)benzaldehyde.

Provenance & Evidence