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In the title compound, C11H12O2, the dihedral angle between the benzene ring and the but-3-en-2-one group is 4.04 (5)°. The crystal packing features chains, parallel to [-101], composed of dimers connected by weak C—H⋯O inter­actions..

The asymmetric unit of the title compound, C14H16ClNO, contains two independent mol­ecules, both with the cyclo­hexene ring in a sofa conformation. In the crystal, N—H⋯O hydrogen bonds link the mol­ecules related by translation along the a axis into two crystallographically independent chains. Weak C—H⋯π inter­actions are also observed.

Indium triflate catalyzed reaction of ketones and aldehydes with malononitrile and acetonitrile provides the title compounds (IV) and (VIII), Subsequent hydrolysis or reduction gives the corresponding carboxylic acids and amines, respectively.