2-Nitrobenzyl alcohol → HCID 89852854, compound

Participants

Reaction Steps

A composition was prepared by mixing 14.4 g (94 mmol) of 2-nitrobenzyl alcohol (Alfa Aesar; Ward Hill, Mass.), 14.6 g (94 mmol) of isocyanatoethyl methacrylate (Aldrich; Milwaukee, Wis.) and 1 drop of dibutyltin dilaurate (Alfa Aesar) in a 4 ounce glass jar. The jar was sealed and placed in an oven set at 70° C. for 2 hours. Analysis of the reaction mixture by infrared (IR) spectroscopy (Nexus 670 FT-IR E.S.P., Thermo Nicolet Corp.; Madison, Wis.) showed no absorbance at 2250 cm−1, indicating substantially no remaining isocyanate functionality. To the cooled reaction mixture were added 40 mL of toluene and the jar was placed in a refrigerator overnight. The next day, white crystals that had formed were filtered off and dried to provide 26.9 g of 2-({[(2-nitrobenzyl)oxy]carbonyl}amino)ethyl 2-methylacrylate (NBMA). The structure of the product was confirmed by NMR and IR spectroscopy analyses.

Provenance & Evidence