Nitrogen → HCID 13426869, compound

Participants

Reaction Steps

In a 3 liter flask equipped with a mechanical stirrer, thermometer, reflux condenser, addition funnel and N2 atmosphere, potassium hydroxide (4.59 mole) was dissolved in methanol (1 L). To the resulting hot solution was added, over a five minute period, methyl 1-methoxybicyclo[2.2.2]oct-5-ene-2-carboxylate (1.53 mole) and the resulting light brown solution was heated to reflux for 5 hours. The reaction was then diluted with H2O (700 ml) and stripped under reduced pressure to a tan slimy solid. This solid was dissolved in fresh H2O (1 L) and washed with methylene chloride (1×500 ml). The separated aqueous layer was acidified to pH 1.5 with 420 ml conc. HCl at reduced temperature and extraced with methylene chloride (3×500 ml). The combined organic layers were washed with H2O (1 L) and brine. Drying and stripping under reduced pressure yielded 87.8% of title product as brown solids; mp 77°-81°; pnmr/CDCl3 /TMS/delta 1.65-2.0 (m, 6, C3H, C7H, C8H), 2.6-2.8 (m, 2, C4H, C2H), 3.4 (s, 3, OCH3), 6.2 (m, 2, C5H, C6H).

Provenance & Evidence