Water → 11-(Benzyloxy)undecylphosphonic acid

Participants

Reaction Steps

Diethyl 11-(benzyloxy)undecylphosphonate (1.00 g, 2.51 mmol) was dissolved in dry dichloromethane (20 mL). Bromotrimethylsilane (1.1 mL, 8.28 mmol) was added via syringe. The reaction was capped with a greased glass stopper and allowed to stir overnight. The volatiles were removed under reduced pressure to yield a yellow oil. This was dissolved in 5:1 methanol:water (20 mL) and allowed to stir 4 hours more. After concentration of the organic, the viscous yellow oil was dissolved in hot acetonitrile and a white crystalline solid was obtained (806 mg, 94% yield). 1H NMR (400.14 MHz, DMSO) δ 7.40-7.20 (m, 5H), 4.43 (2H), 3.39 (t, J=6.49 Hz, 2H), 1.60-1.33 (m, 6H), 1.33-1.15 (m, 14H). 13C{1H} NMR (100.62 MHz, DMSO) δ 138.7, 128.2 (2C), 127.4 (2C), 127.3, 71.79, 69.59, 30.09 (d, J=15.9 Hz), 29.21, 29.04, 29.01, 28.89, 28.87, 28.73, 27.53 (d, J=136.6 Hz), 25.72, 22.72 (d, J=4.6 Hz). 31P{1H} NMR (161.97 MHz, DMSO): δ 27.71. Analysis calculated (found) %: C 63.14 (62.87), H 9.13 (9.13). MS (ESI, m/z): 341 (M−, 100%). Exact mass calculated (found) for [M−H]−, m/z): 341.188722 (341.189600).

Provenance & Evidence