Nitrogen → 4-Methylphenyl isocyanate

Participants

Reaction Steps

Ethylene glycol was reacted with boron trichloride to form the borane compound of formula ##STR32## (For detailed procedure see Genmarie et. al., Tetrahedron Letters, 1984, 25, 2279). To a solution of p-tolyl methyl urethane there were added the borane compound and triethylamine and the mixture was refluxed for 5 minutes (N2 atmosphere). An instantaneous reaction was observed and a white cloudy suspension appeared in the reaction flask, due to the formation of Et3NH+Cl-. p-Tolyl isocyanate was obtained and IR spectra showed the complete disappearance of urethane moieties and the formation of isocyanate moieties.

Provenance & Evidence