Benzoic Acid → Cyano-(2,3-dihydro-5,6-dimethoxy-3,3-dimethyl-1H-inden-1-ylidene)acetic Acid Ethyl Ester

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Reaction Steps

122 g (0.55 mol) of 2,3-Dihydro-5,6-dimethoxy-3,3-dimethyl-1H-inden-1-one (CAS N.[4136-26-9] for preparation see F. Camps, Z. Naturforsch., B : Anorg. Chem., Org. Chem. (1984), 39B (12), 1801-5), 63,3 g (0.56 mol) of ethyl cyano acetate, 12 g (0.14 mol of piperidine, 12 g (0.1 mol) of benzoic acid and 1000 ml toluene were mixed together and heated under reflux for 48 hours. The reaction mixture was cooled to room temperature, washed with diluted HCl, aqueous Na2CO3, and water and then dried (MgSO4). Removal of the solvent and crystallization from EtOH gave 123.8 g of a yellow solid (m.p.: 148-149° C). Yield: 71%; E1%cm: 790 (1 max.: 367 nm) in EtOH. Solubility: 0.35% in CÉTIOL LC

Provenance & Evidence