Propionic Acid → Methyl (4E)-4-methyl-5-(4-methylphenyl)-4-pentenoate

HRID 2408240

Reaktionsgleichung

Reaktionsgleichung von HRID 2408240
[C:1](OC)([O:5][CH3:6])([O:3]C)[CH3:2].[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16](O)[C:17]([CH3:19])=[CH2:18])=[CH:12][CH:11]=1.C(O)(=O)CC>CO>[CH3:19]/[C:17](=[CH:16]\[C:13]1[CH:12]=[CH:11][C:10]([CH3:9])=[CH:15][CH:14]=1)/[CH2:18][CH2:2][C:1]([O:5][CH3:6])=[O:3]

Komponenten

5

Edukt 3

HCID 1032Propionic AcidHCID 15050Trimethyl orthoacetateHCID 540233242-Methyl-1-(4-methylphenyl)prop-2-en-1-ol

Produkt 1

HCID 58390609Methyl (4E)-4-methyl-5-(4-methylphenyl)-4-pentenoateAusbeute 40,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Trimethyl orthoacetate (273 g, 2.24 mol) and 1-(4-methylphenyl)-2-methyl-2-propen-1-ol (91.4% pure, 39.92 g, 0.224 mol) were heated in the presence of propionic acid (0.5 ml) in an oil bath at 120°-150° C. The methanol formed during the reaction was distilled first, followed by the excess orthoacetate. The product was then freed from residual orthoacetate under vacuum and purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 25:1 to 5:1), followed by bulb-to-bulb distillation (100° C./0.001 mbar). 19.62 g (yield=40%) of the desired product were obtained.

Aufarbeitung

  1. distillationwas distilled first
  2. custompurified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 25:1 to 5:1)
  3. distillationfollowed by bulb-to-bulb distillation (100° C./0.001 mbar)

Quellen und Nachweise

ORD-Eintrag
ord-cd845f9f9f244c17a0c39285d6b8c628
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815792B2

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