Furfural → 12-(2-Furyl)-11-dodecenoic acid

Participants

Reaction Steps

This compound was synthesized from 10-carboxydecyltriphenylphosphonium bromide (10.50 g, 20 mmol) and furfural (1.92 g, 20 mmol) in THF (100 mL) by a Wittig reaction. Crystallization afforded the product (2.38 g, 45%) as pale yellow crystals (mp 38-39° C.); IR: 3450-2500, 1715, 695 cm-1 ; 1H-NMR: 1.35 (m, 14 H), 2.35 (t, 4 H), 5.60 (m, 1 H), 6.30 (m, 3 H), 7.35 (s, 1 H), 9.40 (bs, 1 H). Anal. Calcd. for C16H24O3 : C, 72.69, H, 9.15; Found: C, 72.44, H, 9.06%. Z:E=43:57.

Provenance & Evidence