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International Union of Crystallography, Acta Crystallographica Section E: Structure Reports Online, 9(70), p. o897-o898, 2014

DOI: 10.1107/s1600536814015803

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Crystal structure of ethyl 2-(di­eth­oxy­phosphor­yl)-2-(2,3,4-tri­meth­oxy­phen­yl)acetate

Journal article published in 2014 by Moritz Schubert, Dieter Schollmeyer, Siegfried R. Waldvogel ORCID
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

The title compound, C17H27O8P, was prepared by Michaelis–Arbuzov reaction of ethyl 2-bromo-2-(2,3,4-trimethoxyphenyl)acetate and triethyl phosphite. Such compounds rarely crystallize, but single crystals were recovered after the initial oil was left for approximately 10 years. The bond angle of thesp3-hybridized C atom connecting the benzene derivative with the phospho unit is widened marginally [112.5 (2)°]. The terminal P—O bond length of 1.464 (2) Å clearly indicates a double bond, whereas the two O atoms of the ethoxy groups connected to the phosphorous atom have bond lengths of 1.580 (2) Å and 1.581 (3) Å. The three methoxy groups emerge out of the benzene-ring plane due to steric hindrance [C—C—O—C torsion angles = −179.9 (3)°, −52.9 (4)° and 115.3 (4)°]. In the crystal, inversion dimers linked by pairs of C—H...O=P hydrogen bonds generateR22(14) loops. The chosen crystal was modelled as a non-merohedral twin.