1,3-Pentadiene, 2-methyl- → HCID 20035398, compound

Participants

Reaction Steps

A mixture of 82 g (1.0 mol) of 2-methyl-1,3-pentadiene and 92.3 g (0.65 mol) of ethyl trans-4-methyl-2-pentenoate was heated at 175°-185° C. in an autoclave for 6 hours. After cooling, the reaction mixture was distilled. 57 g were obtained of the desired compound as a mixture of approx. 60% cis-trans- and 40% trans-trans-isomer. b.p.: 90°-91° C./0.7 kPa, NMR (cis-trans-isomer): 0.75 (3H, d, J=7 Hz); 0.8-1.0 (6H, d.d., J=7 Hz); 1.25 (3H, t, J=7 Hz); 1.64 (3H, broad s); 1.5-2.6 (6H); 4.09 (2H, k, J=7 Hz); 5.30 (1H). NMR (trans-trans-isomer): 0.8-1.0 (9H, 3xd, J=7 Hz); 1.27 (3H, t, J=7 Hz); 1.64 (3H, broad s); 1.5-2.6 (6H); 4.13 (2H, m); 5.12 (1H).

Provenance & Evidence