Naphthalene → 1,3-Dioxolan-2-one, 4-hexyl-

Participants

Reaction Steps

A 5 mL volumetric flask was charged with 1.5 mL of 1,2-epoxyoctane (1a, 10 mmol), 89 mg of NBS (0.5 mmol), 0.12 g of benzoyl peroxide (0.5 mmol), and 0.13 g of naphthalene (1.0 mmol). The volumetric flask was filled to the mark with anhydrous DMF (2 M). An 8 mL, stainless steel Harvard Apparatus syringe was filled with the solution and then attached to the flow apparatus (syringe pump). The flow apparatus itself was set up as described above. After approximately 4 tR's (˜2 h), a sample was taken using the 6-way valve. The sample was analyzed by GC and 1H NMR. GC analysis indicated 96% conversion whereas 1H NMR analysis indicated a yield of 87% of the title compound 2a. IR (neat): 2928, 2859, 1788, 1384, 1165, 1059, 774 cm−1. 1H NMR (400 MHz, CDCl3): δ 4.67 (qd, J=7.5, 5.5 Hz, 1H), 4.50 (t, J=8.1 Hz, 1H), 4.04 (dd, J=8.3, 7.3 Hz, 1H), 1.79-1.73 (m, 1H), 1.68-1.61 (m, 1H), 1.45-1.27 (m, 10H), 0.86 (t, J=6.9 Hz, 3H). 13C NMR (100 MHz, CDCl3): δ 155.1, 77.1, 69.4, 33.9, 31.5, 28.8, 24.3, 22.5. HRMS (DART) m/z calcd for C9H20NO3 [M+NH4]+: 190.1438. Found: 190.1438.

Provenance & Evidence