Identifying Compounds in Benzoic Acid-Methanol Conversion

[zmike]

My experiment converted Benzoic acid to methyl benzoate using methanol but after adding sodiumbicarb. ether, I am not quite sure what is in where.

Is there methanol or ethanol in the ether layer? since I've read that sodium Carbonate (not bicarb) will not be soluble in ethanol would this mean that ethanol must be in the ether layer?
and what else would be in the bicarb layer?

thanks

 

[Borek]

What is the goal of the experiment?

Bicarbonate is a weak base.

 

[aroc91]

My experiment converted Benzoic acid to methyl benzoate using methanol but after adding sodiumbicarb. ether, I am not quite sure what is in where.

Is there methanol or ethanol in the ether layer? since I've read that sodium Carbonate (not bicarb) will not be soluble in ethanol would this mean that ethanol must be in the ether layer?
and what else would be in the bicarb layer?

thanks

After the esterification, you're left with methyl benzoate in your organic ether layer and everything else in your inorganic (water) layer. Excess methanol should be in the water layer as well as any leftover sodium bicarbonate. Remember that ethanol and methanol are miscible in water.

 

[zmike]

Thank you for the quick replies,
I heard that if you used ethanol instead that some of the ethanol ends up in the ether layer so I thought the same would have happened with the methanol.

 

[aroc91]

I wouldn't doubt that it would, but not to any significant extent.

 

[Ygggdrasil]

When one performs these types of reactions, one reagent is generally in excess to drive the reaction to completion. Did you use excess benzoic acid or excess methanol? Ideally one would use excess benzoic acid since it is easier to separate the unreacted benzoic acid from the methyl benzoate than to separate the methyl benzoate from the unreacted methanol.

 

[Nemus]

You have most of the methanol in the lower water layer. Some will dissolve in the ether but that is normally not a problem because both are low boiling and will go when the ether is evaporated. Remember to add a drying agent first though. Prefereably MgSO4 or, less efficient, Na2SO4. Ether dissolves about 7% water.