Like you know NaBH4 doesn’t hydrogenate esters to alcohols.
What’s my problem? I want to reduce esters (aliphatic and aromatic) to alcohols without using LiAlH4.
Will NaBH4 at least reduce the ester to a aldehyde and alcohol? Like when we use DIBAH? Then the aldehyde can be turn to alcohol by reacting with
NaBH4 and H3O(-).
I heard about activating NaBH4 by adding NiCl2. Apparently using this method the –CN group is quickly reduce to –NH2. Normally NaBH4 doesn’t
reduce –CN. I wonder if it works for the esters.
Maybe someone has more certain information about hydrogenation of esters without LiAlH4?guaguanco - 18-1-2004 at 22:56
Quote:
Originally posted by Mike
Will NaBH4 at least reduce the ester to a aldehyde and alcohol? Like when we use DIBAH? Then the aldehyde can be turn to alcohol by reacting with
NaBH4 and H3O(-).
I don't think so; Esters are stable little suckers.
A google search revealed some catalytic techniques that are out of reach of the home chemist. An old-school route would be:
ester -> acid -> acid chloride -> aldehyde -> alcohol, but I know you're looking for something easier.
What ester are you trying to reduce?Mike - 19-1-2004 at 00:42
Actually I want to: benzoic acide =>methyl benzoate=>benzyl alkohol
Any ideas?
To make an acid chloride I will need SOCl2 wich I can't get. The only hope is
in that NaBH4/NiCl2 way.guaguanco - 19-1-2004 at 13:48
The only hope is
in that NaBH4/NiCl2 way.