alpha-Pinene, (+)- → (E)-(S)-2-Methyl-4-(2,2,3-trimethylcyclopent-3-en-1yl)-2-buten-1-ol

HRID 1604204Notes

Reaction equation

HRID 1604204 reaction equation
[CH3:1]/[C:2](=[CH:5]\[CH2:6][C@@H:7]1[CH2:11][CH:10]=[C:9]([CH3:12])[C:8]1([CH3:14])[CH3:13])/[CH:3]=[O:4].CC1[C@@H]2C(C)(C)[C@@H](C2)CC=1>>[CH3:1]/[C:2](=[CH:5]\[CH2:6][C@@H:7]1[CH2:11][CH:10]=[C:9]([CH3:12])[C:8]1([CH3:14])[CH3:13])/[CH2:3][OH:4]

Participants

3

Reactant 2

HCID 82227alpha-Pinene, (+)-HCID 15330881(E)-(S)-2-Methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-2-buten-1-al

Product 1

HCID 15330882(E)-(S)-2-Methyl-4-(2,2,3-trimethylcyclopent-3-en-1yl)-2-buten-1-olYield 80%

Procedure

(E)-(S)-2-Methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-2-buten-1-al synthesized from (1R,5R)-α-pinene having an optical purity of 97% e.e. (available from Aldrich) was hydrogenated in the same manner as in Example 1 to obtain 3.08 g (yield 80%) of the title compound. The chemical purity of the product was found to be 98% by GC.

Sources & evidence

ORD record
ord-0642cc5a028b482bba257ce1fc0e9ba2
Source dataset
uspto-grants-1999_11
Patent number
US05994291

Reaction notes

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