Methyl Methacrylate → cis,cis-9,12-Octadecadienyl methacrylate

Participants

Reaction Steps

The method of Example 1 was substantially repeated with cis,cis-9,12-octadecadien-1-ol (25.0 g, 9.38 mmol), methyl methacrylate (40 mL, 38 mmol), phenothiazine (0.1 g), and tetraisopropyl titanate (1 mL). When the head temperature rose to 99° C. (pot 112° C.), the reaction mixture was cooled. The material was filtered through activity grade I alumina (30 g, Woelm), and the column was rinsed with ethyl acetate. The combined filtrates were concentrated on a rotary evaporator, finally down to 0.5 mm, to give 32.4 g of light-yellow cis,cis-9,12-octadecadienyl methacrylate. Analysis by HPLC (dichloromethane:ethyl acetate:isopropyl alcohol, 90:10:1, silica gel column) showed that no unreacted octadecadienol was present. 90 MHz 1H NMR: δ 6.03 (1H, broad s, methacrylate vinyl), 5.47 (1H, m, methacrylate vinyl), 5.30 (4H, m, vinyl), 4.09 (2H, t, J=7, OCH2), 2.75 (2H, broad t, J~6, doubly allylic CH2), 2.2-1.1 (27H, m), and 0.89 (3H, t, J~6, --CH2CH3). The NMR spectrum indicated the presence of about 10 mole % methyl methacrylate.

Provenance & Evidence