Chloromethyl Methyl Ether → 3-(Chloromethyl)-2-hydroxy-5-nitrobenzaldehyde

Participants

Reaction Steps

A mixture of 12.0 g of 5-nitrosalicylaldehyde and 100 ml of chloromethyl methyl ether was cooled on an ice bath, and 43.9 g of anhydrous aluminum chloride was added portionwise to said mixture, and the resultant mixture was stirred at room temperature for 10 minutes and then heated under reflux for 22 hours. Then, the reaction mixture was cooled on an ice bath and 200 ml of water was added thereto with vigorous stirring, whereupon white crystals precipitated out. These white crystals were taken out and dissolved in hot hexane, and the solution was filtered, and the mother liquor was cooled to give 14.9 g of 3-chloromethyl-5-nitrosalicylaldehyde as colorless needles (yield 72%).

Provenance & Evidence