Reaction work up question for making benzaldehyde.

[Jack]

I am interested in performing a reaction for the synthesis of benzaldehyde via the oxidation of benzyl alcohol which involves using a mixture of catalytic pyridine and trichloroisocyanuric acid as oxidant, using sodium bicarbonate as base, here is the experimental procedure;

sodium bicarbonate (0.25 g, 3.0 mmol, 1.2 eq.) was suspended in DMF and stirred for 30 minutes under a nitrogen atmosphere. An ambient temperature was maintained by external cooling using a water bath. Subsequently, the alcohol (2.5 mmol, 1.0 eq.) and pyridine (30 μL, 0.37 mmol, 15 mol%) were added. Next a solution of TCCA (0.25 g, 1.1 mmol, 0.43 eq.) in DMF (2.5 mL) was gradually added over 30 minutes using a syringe pump. The resulting mixture was stirred for the appropriate reaction time, A sample was then filtered, diluted with isopropanol and analyzed by GC.

The oxidation of alcohols with trichloroisocyanuric acid: pyridine from base to organocatalyst - Catalysis Science & Technology (RSC Publishing) DOI:10.1039/C2CY20403G

After filtering the reaction mixture to remove the sodium bicarbonate, I am considering adding brine to separate the aqueous phase however the polar aprotic solvent (dimethylformamide) dissolves the benzaldehyde presumably. I am wondering how a chemist would approach isolating the benzaldehyde.

 

[WillD]

Dilute DMF with water, after extraction with ethyl acetate and evaporate.