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3rd January 2013 @ 05:39
Reaction Scheme

2,5-hexanedione (5 g, 5.14 mL, 43 mmol, 1 equiv.) and ammonium carbonate (8.3 g, 86 mmol, 2 equiv.) was heated at 100 ˚C (melts at 86 ˚C) until effervescence stopped (90 mins). Then heated to 115 ˚C for 30 mins. Stirred overnight whilst cooling to room temp. Top layer of orange oil filtered off and bottom layer of orange liquid extracted with chloroform (2 mL). Combined organic layers were dried over CaCl2 under nitrogen and then decanted into a 25 mL round-bottomed flask and purified by distillation at the high vac. Chloroform was removed at room temperature and the product was collected as a clear and colourless distillate (2.41 g, 25.4 mmol, 59% yield) at 68-70 ˚C.

NMR Data:
AEW 32-1.zip
AEW 32-1carbon.pdf
AEW 32-1proton.pdf


Hazard and Risk Assessment:
AEW 32-1.zip


InChi:
InChI=1S/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3
converted to
InChI=1S/C6H9N/c1-5-3-4-6(2)7-5/h3-4,7H,1-2H3

N.B. Product quickly decomposes: store in inert atmosphere in absence of light. Stored in fridge, under Ar and wrapped in Al foil turned from clear and colourless to orange in 1.5 days - freshly distill in future

Reference for preparation:
http://www.lookchem.com/Chempedia/Chemical-Technology/Organic-Chemical-Technology/16247.html
Attached Files
AEW 32-1.png
AEW 32-1proton.pdf
AEW 32-1carbon.pdf
AEW 32-1.zip
HIRAC AEW 32-1.pdf