Pyridine → (E)-3,7-dimethylocta-2,6-dienyl 2-chloroacetate

Participants

Reaction Steps

Geraniol [1] (1.542 g, 10 mmol), succinic anhydride (1.201 g, 12 mmol) and 4-DMAP (10 mg, cat) were suspended in anhydrous dichloromethane (50 ml) under an atmosphere of dry nitrogen. Pyridine (0.791 g, 10 mmol) was added and the reaction mixture was stirred for 24 hrs at room temperature. The reaction mixture was successively washed with 2N HCl and H2O, dried over Na2SO4 and the solvent was evaporated. Remaining volatile material was removed under reduced pressure (0.01 mbar) to yield product [2] as yellow liquid in 99% yield. The product was pure according to 1H NMR and directly subjected to the next step without further purification. 1H-NMR (300 MHz, d6-DMSO) δ(ppm)=12.24 (br s, 1H), 5.29 (t, J=7.0 Hz, 1H), 5.08 (t, 6.7, 1H), 4.55 (d, J=7.1 Hz, 2H), 2.49 (m, 2H), 2.03 (m, 4H), 1.67 (s, 3H), 1.66 (s, 3H), 1.59 (s, 3H). 13C-NMR (75 MHz, d6-DMSO) δ(ppm)=173.3, 172.2, 141.2, 131.1, 123.7, 118.5, 60.7, 38.9, 28.7, 28.6, 25.8, 25.5, 17.5, 16.1.

Provenance & Evidence