I have searched for a cheap and affective method of removing the Hydroxyl group from eugenol.
But with no luck i came across a method in vogels where dilute H2SO4 chilled below 0C is added to chilled hydroxybenzene which, then a halogen was added great!. But im doing this method as i type and im having doughts. In theory the ph should rise from around 2-3 to up near 5-6 as the H2SO4 is consumed but the ph is still around 3?. (the above vogels method was modified to only romove OH)
Any thoughts
Keep in mind i am searching for a method to
?
eugenol-------->(and or) methyallylbenzene/allylbenzene
?
im not sure if i understand you right but your hoping to remove the hydroxy by protonating it to water and having a halogen replaced it by sn2 or sn1, like what would happen for an ordinary alcohol. This type of reaction does normally work on aryl systems.
In general terms the C bearing the LG needs to the sp3 hybridised in order for these reactions to occur.
This is important since students often want to make use of nucleophilic substitution reactions of vinyl or aryl systems which are not generally effective.
The reasons for this are that the adjacent p bonds are electron rich and will repel the Nu- and / or that the vinyl and phenyl carbocations are not very favourable
No i wish to remove the hydroxyl group all together the halogen addition was in the vogel method. But it dont matter because after sitting in the freezer for two weeks i came back and there were two layers one water containing white crystals(a sulphate of some sort i hope) and a top layer of oil (methylallylbenzene i hope) but wont be confermed till next week when a scanning UV/VIS is avalible to see if the hydroxyl group is gone
Here are two methods to remove the OH fromyour compound, save from using the Phosphorous acids and the thionyl route, and of course the use of Zinc-chloride + HCl.........java
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i came across a method in vogels where dilute H2SO4 chilled below 0C is added to chilled hydroxybenzene which, then a halogen was added great!. But im doing this method as i type and im having doughts. In theory the ph should rise from around 2-3 to up near 5-6 as the H2SO4 is consumed but the ph is still around 3?. (the above vogels method was modified to only romove OH)
