Myrcene → (Z)-2,6-dimethyloct-2-ene-1,8-diol

HRID 128146

Reaktionsgleichung

Reaktionsgleichung von HRID 128146
CC(C)=CCCC(C=C)=C.ClC(CCCCC)C(Cl)=C(C)C.C([O:26][CH2:27]/[CH:28]=[C:29](\[CH2:31][CH2:32][CH:33]=[C:34]([CH3:36])[CH3:35])/[CH3:30])(=O)C.C([O-])(=[O:39])C.[Na+].[OH-].[Ca+2].[OH-]>C1C=CC=CC=1.C(N(CC)CC)C>[OH:39][CH2:36]/[C:34](=[CH:33]\[CH2:32][CH2:31][CH:29]([CH2:28][CH2:27][OH:26])[CH3:30])/[CH3:35]

Komponenten

8

Edukt 5

HCID 31253MyrceneHCID 517045Sodium AcetateHCID 1549025Neryl acetateHCID 6093208Calcium HydroxideHCID 20571628Dichloro di-methyloctene

Produkt 1

HCID 77134639(Z)-2,6-dimethyloct-2-ene-1,8-diol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Prod.: (many methods) e.g. from Myrcene, via Myrcene dihydrochloride to Dichloro di-methyloctene. This is converted to Chloro di-hydrogeranyl acetate (and-neryl acetate) with Sodium Acetate in Benzene in presence of Triethylamine. The acetates are saponified with Calcium hydroxide to yield Hydroxycitronellol, from which the aldehyde is prepared by oxidation.

Quellen und Nachweise

ORD-Eintrag
ord-556bbc3a328e454ab039bc372f2aeabf
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04258727

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