Triethyl phosphite → Phosphinecarboxylic acid, diethoxy-, 4-methoxyphenyl ester, oxide

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Reaction Steps

18.6 g (0.12 mole) of triethylphosphite was heated at 125°-130° in a flask with a reflux condensor. 18.6 g (0.10 mole) of 4-methoxyphenyl chloroformate (prepared according to M. J. Zabik and R. D. Schuetz, J. Org. Chem. 32 (1967) 300) was added dropwise. The reaction flask was heated additionally at about 120° for 11/2 hours and left at room temperature overnight. The product was distilled to give 25.8 g (89%) of diethyl 4-methoxyphenoxycarbonylphosphonate. B.p.0.03 174°-8°, nD21 1.4940. Analysis for C12H17O6P. Found (calculated): C 49.79 (50.00), H 6.01 (5.95), P 10.54 (10.75). NMR (CDCl3)δ: 1.42 (t, CH3), 3.78 (s, OCH3), 4.13-4.63 (CH2), 6.77-7.33 (aromatic). IR (neat) cm-1 : 1740 (CO), 1275, 1255, 1190, 1030.

Provenance & Evidence