Sulfuric Acid → HCID 11346391, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the crude alcohol 2 (53 g) in toluene (500 mL) was added silica gel coated with sulfuric acid (3%, 14 g). The mixture was heated to 100° C. and monitored by TLC (prod Rf (25 EA/hex)=0.58). After three hours, the mixture was filtered. The organic phase was washed with water and sodium bicarbonate solution, dried (Na2SO4), and evaporated to give the alkene 3 (42 g, 84%) as a pale-brown solid. TLC Rf (25 EA/hex)=0.58. GC-MS Rt=13.55 min, m/z=274 (M+). 1H NMR (CDCl3, δ): 7.4-6.7 (m, 7H), 6.54 (d, J=9.6 Hz, 1H), 6.0 (m, 1H), 4.08 (t, J=8.0 Hz, 1H), 2.7 (m, 1H), 2.5 (m, 1H). 13C NMR (CDCl3, δ, mult): 143.6, 136.3, 133.8, 132.2, 130.2, 130.2, 128.1, 127.7, 127.2, 126.4, 129.7, 127.4, 42.8(1), 31.6(2).

Provenance & Evidence