Pyridine → Carbonochloridic acid, (9Z)-9-octadecen-1-yl ester

Participants

Reaction Steps

Oleyl alcohol (17.58 g, 65.40 mmol), and triphosgene (6.47 g, 21.80 mmol) were dissolved in 180 ml dichloromethane, stirred and cooled on an ice bath. Anhydrous pyridine (5.17 g of, 65.40 mmol) was added dropwise into the pre-cooled solution. The reaction mixture was stirred for an additional 2 h at room temperature, and then quickly extracted with ice water. The organic layer was combined, dried over Na2SO4 and evaporated to giving crude 18.25 g (84.3% yield) of oleyl chloroformate as liquid. 1H NMR in CDCl3: δ0.88 (t, 3H, J=6.3 Hz, CH3), 1.29 (d, 22H, J=7.7 Hz, CH2), 1.73 (t, 2H, J=6.6 Hz, βCH2), 2.02 (d, 4H, J=5.4 Hz, —CH2—CH═CH—CH2—), 4.31 (t, 2H, J=6.6 Hz, αCH2), 5.35 (m, 2H, —CH═CH—).

Provenance & Evidence