Carbon Dioxide → HCID 13454954, compound

Participants

Reaction Conditions

Reaction Steps

In a nitrogen atmosphere, a solution of 1-bromo-5-(1-methylethenyl)-naphthalene [14.21 g, described by W. F. Short and H. Wang, J. Chem. Soc., 991 (1950)] in diethyl ether (140 ml) was added dropwise to a mixture of ethyl magnesium bromide (prepared from 2.94 g of magnesium and 4.29 ml of ethyl bromide) in diethyl ether (30 ml) at 0° C. The mixture was stirred at 20° C. for 18 hr and then heated at reflux for 1 hr. The cooled solution was poured onto an excess of solid carbon dioxide. The mixture was dissolved in diethyl ether. The resulting solution was washed with a 2N aqueous solution of H2SO4, brine and 10% aqueous NaHCO3 (4x). The basic washes were combined and made acidic (pH 3) with 6N aqueous HCl. The resulting solid was collected, washed with water and dried to give 9.7 g of the title compound; mp 138°-140° C.; NMR(CDCl3) δ 2.15 (s, 3H), 5.0 & 5.38 (2s, 2H), 8.0 (m, 6H), 10.75 (s, 1H).

Provenance & Evidence