反応 #52242

反応方程式

maleimide

Maleimide

formaldehyde

NaOH

→

Hydroxy Methylmaleimide

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   その他an exothermic reaction
3. 3
   workup.WAITThe solution was placed in a freezer overnight
4. 4
   ろ過the resulting crystals filtered
5. 5
   洗浄washed with ice cold ethanol and diethyl ether
6. 6
   その他The white crystals were purified twice by sublimation

実験手順

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).

出典