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84869699134
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A catalytic amount of toluenesulfonic acid (1% mmol in 5 mL of toluene) was added to a solution of D-sorbitol (0.18 g, 1 mmol) in 60 mL of toluene via syringe, under a positive pressure of nitrogen. The solution was heated to reflux overnight and cooled, and the solution was treated with 10 mg of NaHCO3. The particulate matter was subsequently removed by filtration and washed with diethyl ether (10 mL, The toluene filtrate was concentrated in vacuo without heat to give 1,6-anhydrosorbitol 7 as a pale red waxy solid (129 mg, 0.786 mmol, 79, Mp, 29-30°C.1H NMR (CD 3OD):δ 4.54 (t, J, 4.7 Hz, 1H, 4.38 (d, J, 3.7 Hz, 1H, 4.28 (dt, J, 5.4, 6.9 Hz, 1H, 4.2 (s, 1H, 3.9-3.8 (m, 3H, 3.45 (dt, J, 7.5, 8.3 Hz, 1H, 13C NMR (CD3OD, δ 88.3, 81.9, 76.2, 75.2, 72.2, 71.4. MS (EI) m/z 164, 147, 129, 111-102, 87, 69
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3OD): δ 88.3, 81.9, 76.2, 75.2, 72.2, 71.4. MS (EI) m/z 164, 147, 129, 111-102, 87, 69.
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