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blogfast25
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Quote: Originally posted by The Volatile Chemist  | Understandable. It's like, 5:00pm there, right?
Anyways,would the method I proposed actually hydrate both double bonds? I don't exactly follow the discussion about the requirements for primary,
secondary, etc. carbons in the bond. |
I'm not that much of an OC, I'm afraid, certainly not at the practical level.
From what I understand the 1-ene is much more reactive than the hexenyl double bond. But hydration of the latter does also occur but to a lesser
extent. The molecule to the right is alpha-terpineol. Look at the beta and gamma isomers: they are the product of hydration of that hexenyl double bond.
That's why I'm looking into hydrohalogenation (instead of acid-catalyzed hydration) because it appears to be more selective to the 1-ene
bond.
[Edited on 22-1-2016 by blogfast25]
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blogfast25
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Ok, so the procedure in the solvolysis paper (K.N.Gurudutt et al., thanks Solo, for retrieving it) is:
Not a fantastic yield but easy enough and not too long.
The actual solvolysis (conversion of the chloride to carbinol), with 80 % aqueous acetone and ZnO, requires 6 hours of refluxing
though (Table 2.). Hmmm... there's got to be a better way.
[Edited on 22-1-2016 by blogfast25]
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