[H-].C([Al+]CC(C)C)C(C)C.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2([C:22]#N)[CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:13]=1.Cl.CC[O:27]CC>CCCCCC>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2([CH:22]=[O:27])[CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:13]=1A 1M solution of diisobutylaluminium hydride in hexane (100 ml) was added dropwise to a stirred solution of 1-(4-chlorophenyl)cyclobutanecarbonitrile (19.1 g) in dry ether (50 ml) at -30° C. under nitrogen. The mixture was allowed to warm to 0° C. and was kept at that temperature for 30 minutes. The mixture was cooled to -30° C. and 5N hydrochloric acid (100 ml) was added dropwise with stirring. The mixture was filtered to separate a solid and the filtrate was extracted with ether. The solid was added to the ether extracts which were washed with water and dried. Removal of the solvent gave 1-(4-chlorophenyl)cyclobutanecarbaldehyde as a yellow oil.
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