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Pentanal → 3-pentylidene-5-n-butyldihydro-2(3H)-furanone

HRID 36776
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 36776
[CH:1](=O)[CH2:2][CH2:3]CC.[C:7]([CH:10]1[CH2:14][CH2:13][O:12][C:11]1=[O:15])(=O)[CH3:8].[C:16]([CH:19]1[CH2:23][CH:22]([CH2:24][CH2:25][CH2:26][CH3:27])[O:21][C:20]1=[O:28])(=O)[CH3:17].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH:7](=[C:10]1[CH2:14][CH2:13][O:12][C:11]1=[O:15])[CH2:8][CH2:1][CH2:2][CH3:3].[CH:16](=[C:19]1[CH2:23][CH:22]([CH2:24][CH2:25][CH2:26][CH3:27])[O:21][C:20]1=[O:28])[CH2:17][CH2:1][CH2:2][CH3:3]
KomponentenVersuchsvorschriftQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8063PentanalHCID 106012-AcetylbutyrolactoneHCID 14798Sodium HydroxideHCID 108561723-Acetyl-5-butyloxolan-2-one

Produkt 2

HCID 538259603-pentylidene-5-n-butyldihydro-2(3H)-furanoneHCID 544632913-Pentylidene-dihydro-2(3H)-furanone

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Two reactions were carried out in accordance with the process of the invention using valeraldehyde. For one reaction (Example VI) 3-acetyl-dihydro-2(3H)-furanone was used and for the second reaction (Example VII) 3-acetyl-5-n-butyldihydro-2(3H)-furanone was employed. Both reactions used sodium hydroxide with toluene as the diluent and the reactants were present in essentially equimolar amounts. 3-Pentylidene-dihydro-2(3H)-furanone (86°-104° C. at 0.1 mm/Hg) and 3-pentylidene-5-n-butyldihydro-2(3H)-furanone (110°-131° C. at 0.01 mm/Hg) were obtained from the respective reactions. Proton nuclear magnetic resonance spectra for the products were as follows: 3-Pentylidene-dihydro-2(3H)-furanone: 1HNMR (CDCl3) δ6.7 (m, 0.93H), 6.26 (m, 0.07H), 4.4 (t, 2H), 2.9 (m, 2H) 2.22 (m, 2H), 1.4 (m, 4H), 0.9 (t, 3H). 3-Pentylidene-5-n-butyldihydro-2(3H)-furanone: 1HNMR (CDCl3) δ6.7 (tt, 0.4H), 6.2 (tt, 0.6H), 4.45 (m, 1H) 3.1-1.5 complex multiplets, 14H), 0.9 (two superimposed triplets, 6H).

Quellen und Nachweise

ORD-Eintrag
ord-f9be7422b2ee415887c599b10259adfe
Quelldatensatz
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05416224

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