2-Phthalimidoacetaldehyde Diethyl Acetal → Phthalylglycine aldehyde

Participants

Reaction Steps

Phthalimidoacetaldehyde diethyl acetal (76.40 g, 0.32 mol, Aldrich) was dissolved in 85% formic acid (300 mL) and stirred for 2 h at rt. After TLC analysis indicated full conversion to the aldehyde (Rf=0.34 1:1 hexanes/EtOAc, 2,4-DNP: yellow), the solvent was removed and the residue was dried under vacuum (150 mm Hg) to afford 2-(1,3-dioxoisoindolin-2-yl)acetaldehyde (56.34 g, 93%) as a white solid. 1H NMR: 4.57 (s, 2H), 7.76 (m, 2H), 7.77(m, 2H), 9.66 (s, 1H).

Provenance & Evidence