[CH:1]1([OH:14])[CH2:12][CH2:11][CH:10]=[CH:9][CH2:8][CH2:7][CH:6]=[CH:5][CH2:4][CH2:3][CH:2]1[OH:13].[CH3:15][CH2:16][CH2:17][CH2:18][CH:19]=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[Cl-].[Na+].O>[CH2:16]([CH:15]1[O:13][CH:2]2[CH:1]([CH2:12][CH2:11][CH:10]=[CH:9][CH2:8][CH2:7][CH:6]=[CH:5][CH2:4][CH2:3]2)[O:14]1)[CH2:17][CH2:18][CH3:19]5 g of 5,9-cyclododecadien-1,2-diol, 2.4 g of valeric aldehyde, a spatula of p-toluenesulfonic acid and 200 ml of 80/100 petroleum ether were charged into a 250 ml two-neck flask equipped with a water separator and the mixture was taken to reflux for 1 h. The reaction mixture was then poured on ice, neutralized with brine, dried and concentrated. Distillation in a bulb-to-bulb apparatus produced 6.06 g of 14-butyl-13,15-dioxabicyclo[10.3.0]pentadeca-4,8-diene.
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