Benzene → Methyl atropate

Participants

Reaction Steps

The compound was synthesized according to a literature method (Ames and Davey J. Chem. Soc. 1958, 1798). To a solution of phenylacetic acid methyl ester (13.58 ml, 100 mmol) in 35 ml of benzene was added diethyl glyoxalate (20.72 ml, 130 mmol). The solution was allowed to stir at room temperature for 1 hour at which point a solid mass was obtained. Suspending the mass in ether followed by filtration yielded a white powder. The white powder was then suspended in ether and acidified using 5% HCl. The aqueous layer was then removed and the ether layer was washed with saturated NaHCO3, H2O, and brine, dried over MgSO4 and then concentrated under reduced pressure. The resulting yellow oil was charged with 45 ml of 37% formaldehyde solution (in water) and 100 ml of water at room temperature. 40 g K2CO3 in 50 ml of water was added via addition funnel to the reaction mixture over a period of 30 minutes. The reaction was then stirred for a further 2 hours at room temperature. The resulting mixture was extracted with ether three times, and the resulting ethereal solution was washed with water, brine, dried over MgSO4, and subjected to Kugelrohr distillation (83° C., 0.5 mmHg) to afford the title compound as an oil (81% yield, 14.1 g). 1H NMR (CDCl3, 300 MHz) δ:7.50-7.30 (m, 5H), 6.35 (d, J=1.2 Hz, 1H), 5.90 (d, J=1.2 Hz, 1H), 4.31 (q, J=7.2 Hz, 2H), 1.36 (t, J=7.2 Hz, 3H) ppm.

Provenance & Evidence