Tetrahydrofuran → 4,8-Dimethyldeca-4,7,9-trienal

Participants

Reaction Steps

A solution of 13.4 g. (53 mM) of the C12 -aldehyde diethylacetal, prepared according to the method described in paragraph c), 250 ml. of tetrahydrofuran, 60 ml. of water and and 0.5 ml. of 72% perchloric acid was left for 20 hours at room temperature under nitrogen. Water was added and the mixture was extracted with pentane (3x). The organic layers were washed with 5% NaHCO3 and water, dried over sodium sulphate and evaporated. The remaining oil was distilled to yield 9.2 g. (99%) of 4 methyl-8-vinyl-4,7-nonadienal, b.p. 73°-75°/0.3 Torr. IR(CHCl3): 2720, 1720, 1640, 1605, 995, 905 cm-1. NMR(CCl4): 1.4 - 1.8 ppm (m, 6 H), 2.2 - 2.5 ppm (m, 4H), 2.78 ppm (t, J = 7 cps, 2 H), 4.6 - 5.5 ppm (m, 4 H), 6.20 ppm (about 75%) / 6.64 ppm (about 25%) (2 d of d, J = 10 and 17 cps, 1 H), 9.55 ppm (t, J = about 1.5 cps, 1 H).

Provenance & Evidence