The preparation and crystal structure of tetrakis(phenylmethoxy)methane

Abstract

The new compound tetrakis(phenylmethoxy)methane (also known as benzyl orthocarbonate) has been produced by the action of the sodium salt of benzyl alcohol on trichloronitromethane (chloropicrin), resulting in a white crystalline solid with a melting range of 68–70 °C. The crystal structure has been determined at 153(5) K: triclinic, [Formula: see text], a = 10.161(4) Å, b = 12.664(4) Å, c = 20.472(5) Å, α = 71.78(2)°, β = 82.30(3)°, γ = 71.92(2)°. The results show the symmetry at each central carbon to be approximately S4, with average C—O bond lengths of 1.397(4) Å, O—C—O angles ranging between 113–114° and 107–108°, and C—O—C angles of 115(1)°. Additional evidence for this structure is given by nuclear magnetic resonance, infrared and mass spectra. Keywords: benzyl orthocarbonate, orthocarbonate, tetrakis(phenylmethoxy)methane.