Phthalimide → Phthalimide, N-(2-formylethyl)-

HRID 2298563Notes

Reaction equation

HRID 2298563 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH:12]([CH:14]=[CH2:15])=[O:13].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC>>[C:1]1(=[O:11])[N:5]([CH2:15][CH2:14][CH:12]=[O:13])[C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12

Participants

4

Reactant 3

HCID 6809PhthalimideHCID 7847AcroleinHCID 2723671Tetrabutylammonium Hydroxide

Product 1

HCID 75525Phthalimide, N-(2-formylethyl)-

Procedure

3-Phthalimidopropanal was prepared by addition of phthalimide to acrolein in the presence of tetrabutylammonium hydroxide according to the procedure described by R. O. Atkinson & F. Poppelsdorf, J Chem. Soc. (1952) 2448. 1H-NMR (CDCl3, 400 MHz): δ 9.82 (t, 1H, J=2); 7.85 (m, 2H); 7.72 (m, 2H); 4.04 (t, 2H, J=7); 2.88 (dt, 2H, J=2, 7). 13C-NMR (CDCl3, 100 MHz): δ 199.36, 167.98, 134.10, 131.95, 123.36, 42.35, 31.67.

Sources & evidence

ORD record
ord-5e7aab2d130d4159aa86ffb36a53bae1
Source dataset
uspto-grants-2002_12
Patent number
US06492562B1

Reaction notes

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