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

Participants

Reaction Steps

A 43.9 g (0.33 mole) quantity of anhydrous aluminum chloride was added in small portions to a mixture of 12.0 g (71.8 mmoles) of 5-nitrosalicylaldehyde and 100 ml of chloromethyl methyl ether with cooling in an ice bath. The resulting mixture was stirred at room temperature for 10 minutes and refluxed with heating for 22 hours. Thereafter, the reaction mixture was cooled in an ice bath, followed by addition of 200 ml of water with thorough stirring, whereby white crystals were precipitated. The white crystals were collected, dissolved in hot hexane and filtered. The mother liquor was cooled, giving 14.9 g (yield: 72%) of 3-chloromethyl-5-nitrosalicylaldehyde as colorless needle crystals.

Provenance & Evidence