Hydroquinone → 3',5'-Dimethoxy-2-nitro-1,2,3,6-tetrahydro-1,1'-biphenyl

Participants

Reaction Conditions

Reaction Steps

A stainless steel pressure vessel was charged with 28.6 g. (0.137 mole) 3,5-dimethoxy-beta-nitrostyrene, 20 g. (0.378 mole) butadiene, 40 ml. toluene and a few crystals of hydroquinone. The vessel was cooled to -78° C. under a nitrogen atmosphere and sealed. The sealed vessel was heated at 100° C. for 48 hours, cooled and the reaction mixture concentrated under nitrogen. The residual solid was crystallized from methanol to afford 29.8 g. of title compound, M.P. 80.5°-82° C. J. Org. Chem., 27, 376 (1962) reported M.P. 73°-75° C. 1H-NMR (CDCl3) ppm (delta): 3.75 (s, 6H, OCH3), 4.95 (m, 1H, CHNO2), 5.75 (s, 2H, olefin), 6.40 (s, 3H, aromatic).

Provenance & Evidence