trans-2-Hexenal → 8,10-Tetradecandienoic acid
Reaction equation
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].[CH:31](=O)/[CH:32]=[CH:33]/[CH2:34][CH2:35][CH3:36]>>[C:2]([OH:4])(=[O:3])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH:31][CH:32]=[CH:33][CH2:34][CH2:35][CH3:36]Participants
3
Procedure
This compound was synthesized from 7-carboxyheptyltriphenylphosphonium bromide (9.71 g, 20 mmol) and 2-trans-hexenal (1.96 g, 20 mmol) in 10% hexamethylphosphoric triamide (HMPA)-THF (100 mL) by a Wittig reaction. Kugelrohr distillation yielded the product (1.97 g, 44%) as a yellow oil (bp 123-126° C./0.01 torr). IR: 3450-2500, 1720 cm-1 ; 1H-NMR: 0.95 (t, 3 H), 1.35 (m, 8 H), 1.62 m, 2 H), 2.05 (m, 4 H), 2.32 (t, 2 H), 5.23 (m, 1 H), 5.60 (m, 1 H), 5.90 (m, 1 H), 6.05 (m, 1 H), 10.50 (bs, 1 H). Anal. Calcd. for C14H24O2 : C, 74.95, H, 10.78%; Found: C, 75.01, H, 10.80%.
Workup
- distillationKugelrohr distillation