The Reaction of Aldoketene Dimers with Grignard Reagents1 - The

DOROTHY V. NIGHTINGALE, and ROY H. TURLEY Jr. J. Org. Chem. , 1961, 26 (8), pp 2656–2658. DOI: 10.1021/jo01066a010. Publication Date: August 1961...
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of o-terphenyl, identified by its melting point and an infrared hexene, 5.2 ml. of 88'3, formic acid, and 1.2 ml. of 30%) spectral comparison with an authentic sample. hydrogen peroxide was stirred for 9 hr. a t room temperature. crs-l,&Diphenyl-1 ,&cyclohexanediol (VII). One gram The formic acid was distilled under reduced pressure and (0.0039 mole) of osmium tetroxide was added to a solution the residue was treated with 10 ml. of 20% sodium hydroxide of 0.94 g. (0.0040 mole) of l,%diphenylcyclohexene in 50 ml. solution for 2 hr. on a steam bath. Extraction of the product of ether and 1.5 ml. of pyridine. After 48 hr. at room tem- followed by crystallization from ligroin gave 0.37 g. of glycol perature, the solvent was evaporated. The gummy solid VIII. m.D. 131-133'. was boiled with 6 g. of sodium sulfite in 80 ml. of 50% Clyro