Propyne → beta-Damascenone, (2Z)-

HRID 1579804Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1579804
CC(=CCCC(=CC=O)C)C.C#CC.[CH3:15][C:16]1[CH:21]=[CH:20][CH2:19][C:18]([CH3:23])([CH3:22])[C:17]=1[CH:24]([OH:28])[C:25]#[C:26][CH3:27].CC1C=CCC(C)(C)C=1C(=O)C#CC>O=[Mn]=O>[CH3:15][C:16]1[CH:21]=[CH:20][CH2:19][C:18]([CH3:22])([CH3:23])[C:17]=1[C:24](=[O:28])/[CH:25]=[CH:26]\[CH3:27]

Komponenten

6

Edukt 4

HCID 6335PropyneHCID 88433,7-Dimethylocta-2,6-DienalHCID 233380792,6,6-Trimethyl-1-[1-hydroxy-2-butynyl]-1,3-cyclohexadieneHCID 705879512,6,6-Trimethyl-1-tetrolyl-1,3-cyclohexadiene

Produkt 1

HCID 12309006beta-Damascenone, (2Z)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14801Manganese dioxideKatalysator

Versuchsvorschrift

Safranal, prepared according to Compt. rend. 262, 1725 (1966), was reacted with propyne to give 2,6,6-trimethyl-1-[1-hydroxy-2-butynyl]-1,3-cyclohexadiene, following the procedure outlined in Example 18, paragraph b, for the reaction of citral with propyne. The above carbinol was oxidised with MnO2 to 2,6,6-trimethyl-1-tetrolyl-1,3-cyclohexadiene, following the procedure described in Example 18, paragraph c), for the oxidation of the dihydro analogue. The above acetylenic ketone was then partially reduced to the title compound following the method described in Example 18, paragraph a). Cis-2,6,6-trimethyl-1-crotonoyl-1,3-cyclohexadiene gave the following NMR data (CCl4): 1.06 (6 H, s), 1.69 (3 H, s), 2.09 (2 H, d, J = 2.3 cps), 2.14 (3 H, d, J = 5.5 cps), 5.81 (2 H, t + s, J = 2.3 cps), 6.2 (2 H, complex band) ppm (δ).

Quellen und Nachweise

ORD-Eintrag
ord-fcfbec8a2e1f4f818725a4ab860492ef
Quelldatensatz
uspto-grants-1976_01
Patentnummer
US03931326

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