Since the phenoxide is not purified and contains some starting materials and sin
ID: 513334 • Letter: S
Question
Since the phenoxide is not purified and contains some starting materials and since the alkylation step does not proceed to completion, the red DMSO-toluene solution contains significant amounts of the following compounds: acetophenone, p-hydroxybenzaldehyde, 1-phenyl-3-p-hydroxyphenyl-2-propenone, diethyl aminoethyl chloride and the desired product 1-phenyl-3-p-diethylaminoethoxyphenyl)-2-propene-1-one. Some of these ionic forms.
What compounds are present in significant amount in aqueous layer remaining after the extraction with ether?
What compounds are present in significant amount in the ether layer after extraction with acid?
What compounds are likely to present as significant impurities in the final product?
Explanation / Answer
When final product is extracted with ether, the following material comes into the ether layer (upper layer):-
Acetopheone, p-hydroxybenzaldehyde, 1-phenyl-3-p-hydroxyphenyl-2-propenone and the desired product 1-phenyl-3-p-diethylaminoethoxyphenyl)-2-propene-1-one ( as pe the solubility rule)
And the diethyl aminoethyl chloride will goes into the aqueous layer after the extraction.
After the extraction of the ether layer with acid may cause the neutralization of the ammonium group in the desired product (1-phenyl-3-p-diethylaminoethoxyphenyl)-2-propene-1-one) with acid and may lead to the quaternary ammonium salt and gets precipitated. The desired product may be able to seperate it out from the impurity.