p-Toluenesulfonic acid → HCID 86666522, compound

Participants

Reaction Steps

A solution of iminodiacetic acid 8 (3.0 g, 22.54 mmol), allyl alcohol (18.43 mL, 270 mmol) and p-toluenesulfonic acid (8.57 g, 45.0 mmol) in benzene (60 mL) was heated at reflux with a Dean-Stark distilling trap for 16 h. The mixture was cooled to room temperature and the solvent was evaporated in vacuo. The residue was crystallized from diethyl ether and dried in vacuo to give the compound 9 (8.21 g, 94.6%). 1H NMR (400 MHz, CDCl3) δ 2.34 (s, 3H), 4.17 (s, 4H), 4.61 (d, J=6.2, 4H), 5.24 (d, J=11.7, 2H), 5.31 (d, J=17.2, 2H), 5.82 (m, 2H), 7.15 (d, J=7.8, 2H), 7.68 (d, J=8.2, 2H).

Provenance & Evidence