Sulfuric Acid → HCID 11095317, compound

Participants

Reaction Steps

360 ml. (0.36 mol) 1M DIBAH solution in methylene chloride was added dropwise in the course of 1.5 hours, while cooling to -15° to -10° C., into a solution of 60.5 g. (0.33 mol) o-(1-cyclohexenyl)-benzonitrile in 500 ml. anhydrous diethyl ether, stirred for a further hour at 0° C., subsequently for 3 hours at ambient temperature and decomposed with 5N sulphuric acid. The precipitate obtained was filtered off with suction and the organic phase was washed with an aqueous solution of sodium chloride, dried and evaporated. The aldehyde obtained was used for the following stage without further purification (crude yield 95% of theory). NMR,(60 MHz, CDCl3, ppm): 10.25 (1H, s, --CHO); 6.90-8.10 (4H, m. aromat. protons); 5.70 (1H, m, olef. proton); 1.05-2.50 (8H, m, cyclohexenyl radical).

Provenance & Evidence