Benzyl
In
organic chemistry, benzyl is the term for the radical, ion or
functional group C6H5CH2, which can be obtained formally by removing a hydrogen atom from
toluene's methyl group. The benzyl functional group is sometimes abbreviated "Bn". For example,
benzyl alcohol can be abbreviated to BnOH.
In substituent nomenclature, benzyl and
phenyl are commonly confused. Benzyl can be seen as a phenyl attached to a CH2 before attaching to the parent compound.
Encyclopedia
In
organic chemistry,
benzyl is the term for the radical, ion or
functional group C
6H
5CH
2, which can be obtained formally by removing a hydrogen atom from
toluene's methyl group. The benzyl functional group is sometimes abbreviated "
Bn". For example,
benzyl alcohol can be abbreviated to BnOH.
In substituent nomenclature, benzyl and
phenyl are commonly confused. Benzyl can be seen as a phenyl attached to a CH
2 before attaching to the parent compound.
Benzyl protective groups
Benzyl groups are frequently used in organic synthesis as
protective group for
alcohols and
carboxylic acids.
Two common methods for benzyl ether protection:
The benzyl group can be removed by hydrogenation.
One study employs a benzyl
pyridinium salt as a benzyl donor for alcohols:
The solvent is trifluoromethylbenzene and
magnesium oxide is an acid scavenger. The reaction type for this conversion is believed to be
SN1 based on the detection of trace amounts of
Friedel-Crafts reaction sideproducts with
toluene as a solvent.
References
