Hydrogen Peroxide → (-)-cis-Myrtanol

HRID 865819Notes

Reaction equation

HRID 865819 reaction equation
B.C(SCCC(C)C)CC(C)C.B.COCCS[CH2:19][CH2:20][O:21]C.[CH3:23][C:24]1([CH3:32])[C@H:30]2[CH2:31][C@@H:25]1[CH2:26][CH2:27]C2=C.OO.[OH-].[Na+]>>[CH3:23][C:24]1([CH3:32])[C@H:30]2[CH2:31][C@@H:25]1[CH2:26][CH2:27][C@H:19]2[CH2:20][OH:21]

Participants

6

Reactant 5

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 440967(-)-beta-PineneHCID 178419188HCID 178419188, compound2×HCID 178419212HCID 178419212, compound

Product 1

HCID 11084102(-)-cis-MyrtanolYield 82%

Procedure

Hydroborations on a preparative scale were carried out with borane-diisoamyl sulfide and borane-bis(2-methoxyethyl) sulfide for illustrative purposes. Thus (-)-β-pinene (93% ee) was reacted with borane-diisoamyl sulfide and the organoborane intermediate was oxidized with standard 30% hydrogen peroxide and 3M sodium hydroxide used in excess to suppress oxidation of the sulfide. (-)-cis-Myrtanol was isolated by distillation in 82% yield and the sulfide was recovered.

Sources & evidence

ORD record
ord-7ee0452f2cf8445ab63f4958642a7bbf
Source dataset
uspto-grants-1996_10
Patent number
US05567849

Reaction notes

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