Reaktion #551236

ord-8fb315b99e2b4dc38cf9006f07039521

Reaktionsgleichung

C=C(CC)CC/C=C(\C)CCC=C(C)C
(E)-β-farnesene
C=C(CC)CC/C=C(\C)CCC=C(C)C
product
C=C(CC)CC/C=C(\C)CCC=C(C)C
(E)-β-farnesene
CCOC(=O)/C=C\C(=O)OCC
diethyl maleate
CCOC(=O)C1CC=C(CCC=C(C)CCC=C(C)C)CC1C(=O)OCC
1,2-bis-(ethoxycarbonyl)-4-(4,8 dimethyl-3,7-nonadienyl) cyclohex-4-ene
Ausbeute 75.0%

Reaktionsbedingungen

Temperatur
180°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.DISTILLATIONThe mixture is then distilled under reduced pressure

Vorschrift

The (E)-β-farnesene-containing product of Example 1 (10 g) and diethyl maleate (5.0 g) are heated together at 180° C. for two hours. The mixture is then distilled under reduced pressure to give 1,2-bis-(ethoxycarbonyl)-4-(4,8 dimethyl-3,7-nonadienyl) cyclohex-4-ene as a pale yellow oil (8.5 g, 75%); b.p. 175°-180° C./0.3τ; nD20 1.4894; M+ (m/z as % of base peak): 376 (6.6); δ(CCl4) 1.24 (t, 6H), 1.70 (m, 9H), 2.08 (m, 8H), 2.36 (m, 4H), 2.80 (m, 2H), 4.14 (q, 4H), 5.20 (m, 2H), 5.40 (br, t, 1H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04546110uspto-grants-1985_10