3-tetradec-1-enyloxolane-2,5-dione

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Tetradecenyl succinic anhydride (198 mg, 0.67 mmol) and triethylamine (0.18 ml, 1.29 mmol) were added to a solution of compound 1 (200 mg, 0.64 mmol) in methylene chloride. The reaction mixture was stirred at room temperature for 2 h. The crude compound was passed through silica column, and using 10% methanol:chloroform as eluant, compound 27 was obtained as yellow thick syrup (357 mg, 92% yield). Rf (10:90 methanol:chloroform)=0.31. 1H NMR (300 MHz, CDCl3): δ 7.90-7.80 (m, 3H, 2C═CH, vinyl-H), 7.45-7.00 (m, 9H, Ar—H, vinyl-H), 5.40-4.50 (m, 9H), 2.70-1.70 (m, 9H), 1.40-1.20 (m, 12H), 0.93 (t, 3H, J=6.6, CH3). 13C NMR (75 MHz, CDCl3): δ 186.10, 174.03, 170.76, 162.6 (d, J=51.2), 133.75, 133.55, 132.36, 130.75, 126.68, 124.22 (d, J=9.8), 115.98 (d, J=21.2), 44.75, 32.46, 31.90, 22.67, 14.12. ESI Mass calculated for C37H45F2NNaO4 (M+Na)+628.32. found 628.27.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Seventeen millimoles of tetradecenylsuccinic anhydride (5.0 gm), 34 millimoles of oleyl alcohol (9.1 gm), 50 mg of adipic acid and 10 ml of toluene were combined in a boiling flask (with attached Dean-Stark trap) and refluxed for about 6 hours in the presence of the catalyst p-toluenesulfonic acid. Excess toluene was removed at ambient pressure. The residue was applied to a silica gel column, and eluted with petroleum ether. Elution with petroleum ether gave dioleyl tetradecenylsuccinate. Oleyl alcohol and other impurities were retained on the column. The dioleyl tetradecenylsuccinate has a low melting point and can be used for the commercial production of calorie-reduced fried snack foods. Excess toluene was removed at ambient pressure eluted with petroleum ether Elution with petroleum ether