Acetate → Geraniol nerol

HRID 27395Notes

Reaction equation

HRID 27395 reaction equation
[CH3:1][C:2](Cl)([CH3:10])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]CC.[CH3:12][C:13]([CH3:21])=[CH:14][CH2:15][CH2:16][C:17]([CH:19]=[CH2:20])=[CH2:18].Cl.[C:23]([O-:26])(=[O:25])[CH3:24].[Na+].C([O-])(=O)C.[OH-].[Na+]>>[OH:25][CH2:20]/[CH:19]=[C:17](/[CH3:18])\[CH2:16][CH2:15][CH:14]=[C:13]([CH3:21])[CH3:12].[CH3:1][C:2](=[CH:3][CH2:4][CH2:5]/[C:6](=[CH:24]/[CH2:23][OH:26])/[CH3:7])[CH3:10]

Participants

6

Reactant 5

HCID 175AcetateHCID 14798Sodium HydroxideHCID 1381892-Chloro-2-methylnonaneHCID 517045Sodium AcetateHCID 19805005Myrcene hydrochloride

Product 1

HCID 86588956Geraniol nerol

Procedure

The dimethyloctyl chloride is then obtained by reacting the myrcene hydrochloride (neryl/geranyl chloride) with sodium acetate and saponifying the acetate with sodium hydroxide to produce nerol/geraniol. This is then hydrogenated to produce dimethyloctanol, which is treated with HCl in the presence of zinc chloride to produce the dimethyloctyl chloride.

Sources & evidence

ORD record
ord-5e686666afb648aaaad97f3640882fb7
Source dataset
uspto-grants-1980_09
Patent number
US04221742

Reaction notes

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