Reaktion #52242

Reaktionsgleichung

maleimide

Maleimide

formaldehyde

NaOH

→

Hydroxy Methylmaleimide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Sonstigean exothermic reaction
3. 3
   workup.WAITThe solution was placed in a freezer overnight
4. 4
   Filtrationthe resulting crystals filtered
5. 5
   Waschenwashed with ice cold ethanol and diethyl ether
6. 6
   SonstigeThe white crystals were purified twice by sublimation

Vorschrift

Maleimide (10 g, 0.103 mol) was added to 10 mL of a 37% solution of formaldehyde and 0.31 mL of a 5% solution of NaOH was added. Within 10 minutes all of the maleimide had dissolved and an exothermic reaction proceeded. The solution was stirred for 2 hours where white crystals were observed. The solution was placed in a freezer overnight and the resulting crystals filtered and washed with ice cold ethanol and diethyl ether. The white crystals were purified twice by sublimation. See P. O. Tawney, R. H. Snyder, R. P. Conger, K. A. Leibbrand, C. H. Stiteler, and A. R. Williams J. Org. Chem. 26, 15 (1961). m.p. 104-106° C. (9.77 g, 74.6%). 1H-NMR (Acetone-d6, δ, ppm): 4.96 (2H, —CH2—, s), 5.33 (1H, —OH, s), 6.93 (2H, —CH═CH—, s). 13C-NMR (Acetone-d6, δ, ppm): 60.9 (1C, —CH2—), 135.6 (2C, —CH═CH—), 173.1 (1C, —C═O).

Quelle