Sulfuric Acid → HCID 23044216, compound

Participants

Reaction Steps

10 g (63 mmol) of 5-methoxybenzocyclobutene-1-carboxylic acid nitrile are introduced at -60° C. under argon into 200 ml of tetrahydrofuran. While stirring, 75 ml (75 mmol) of a 1 molar solution of diisobutyl-aluminium hydride in hexane are slowly added dropwise. The reaction mixture is then allowed to warm slowly to room temperature and is stirred for a further 4 hours. At room temperature, 500 ml of saturated ammonium chloride solution are then added and the whole is subsequently stirred for 40 minutes. 220 ml of 5% sulphuric acid are added and extraction is carried out twice with diethyl ether. The combined organic phases are dried and concentrated. The crude product is purified by chromatography on the ten-fold amount of silica gel. 5-methoxybenzocyclobutene-1-carboxaldehyde, Rf=0.23, hexane/ethyl acetate (9:1), is obtained.

Provenance & Evidence