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

HRID 1278445Notes

Reaction equation

HRID 1278445 reaction equation
[CH3:1][C:2]([CH3:10])=[CH:3][CH2:4][CH2:5][C:6]([CH:8]=[CH2:9])=[CH2:7].ClC(CCCCC)C(Cl)=C(C)C.C([O-])(=O)C.[Na+].[OH-:28].[Ca+2].[OH-:30]>C1C=CC=CC=1.C(N(CC)CC)C>[OH:28][CH2:1]/[C:2](=[CH:3]\[CH2:4][CH2:5][CH:6]([CH2:8][CH2:9][OH:30])[CH3:7])/[CH3:10]

Participants

7

Reactant 4

HCID 31253MyrceneHCID 517045Sodium 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 (andneryl 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-25831ef8222949cc9911fc6f4262022b
Source dataset
uspto-grants-1981_07
Patent number
US04281177

Reaction notes

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