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

HRID 128146

Reaction equation

HRID 128146 reaction equation
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]

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8471TriethylamineSolvent

Procedure

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.

Sources & evidence

ORD record
ord-556bbc3a328e454ab039bc372f2aeabf
Source dataset
uspto-grants-1981_03
Patent number
US04258727

Linked notes

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