p-Toluenesulfonic acid → 5-Hexadecene, 16,16-diethoxy-, (5Z)-

HRID 542531

Reaktionsgleichung

Reaktionsgleichung von HRID 542531
[CH:1](=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][CH3:16].CC(=CCC/C(=[CH:26]\[CH:27]=[O:28])/C)C.[CH3:29][C:30](=O)CCCCC.CC1C=CC(S(O)(=O)=O)=CC=1>[NH4+].[Cl-]>[CH2:29]([O:17][CH:1]([O:28][CH2:27][CH3:26])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][CH3:16])[CH3:30]

Komponenten

6

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 80512-HeptanoneHCID 643779NeralHCID 536449511-Hexadecenal, (11Z)-

Produkt 1

HCID 64380175-Hexadecene, 16,16-diethoxy-, (5Z)-Ausbeute 61,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 25517Ammonium ChlorideKatalysator

Versuchsvorschrift

The diethyl acetal or ketal is prepared by the above general procedure from (Z)-11-hexadecenal, (E)-and (Z)-citral in admixture and heptan-2-one using NH4Cl as catalyst in the first two cases and TsOH in the last. (Z)-1,1-Diethoxyhexadec-11-ene is obtained in 61.5% yield and has a b.p. 118°-120°C./0.05 mm, nD20 1.4475; (E)-and (Z)-1,1-diethoxy-3,7-dimethoxyocta-2,6-diene in admixture are obtained in 83.6% yield and have b.p. 68°-70°C./0.2 mm, nD20 1.4511; 2,2-diethoxyheptane is obtained in 71% yield and has b.p. 88°-92°C./18 mm.

Quellen und Nachweise

ORD-Eintrag
ord-b9e4481c70e942cfbd66ddfd7aba01d9
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04657926

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