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

HRID 1905355Notes

Reaction equation

HRID 1905355 reaction equation
[CH3:1][C:2]([CH:4]=[CH:5][CH3:6])=[CH2:3].[CH3:7][CH:8]([CH3:16])/[CH:9]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12]>>[CH3:6][CH:5]1[CH:4]=[C:2]([CH3:3])[CH2:1][CH:9]([CH:8]([CH3:16])[CH3:7])[CH:10]1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

3

Reactant 2

HCID 142381,3-Pentadiene, 2-methyl-HCID 5315066Ethyl (2E)-4-methyl-2-pentenoate

Product 1

HCID 20035398HCID 20035398, compound

Procedure

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).

Workup

  1. temperaturewas heated at 175°-185° C. in an autoclave for 6 hours
  2. temperatureAfter cooling
  3. distillationthe reaction mixture was distilled

Sources & evidence

ORD record
ord-759cbb8caad54d6db68dfd131ba79b9a
Source dataset
uspto-grants-1989_06
Patent number
US04843061

Reaction notes

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