Benzoic acid, 4,4'-carbonylbis-, dimethyl ester → HCID 16086976, compound

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Reaction Steps

A mixture of 6 (2.33 g, 7.81 mmol), HCl-H2NOH (1.63 g, 23.4 mmol) and sodium acetate (1.92 g, 23.4 mmol) in Ethanol (80 ml) was heated for 24 h under reflux. The mixture was allowed to cool to RT, and half concentrated NaHCO3-solution (200 ml) was added. The aqueous phase was extracted with Et2O, the unified organic phases were washed with saturated solutions of NaHCO3 and NaCl, and dried over Na2SO4. The solvent was removed, and the crude product is crystallized from ethanol. 2.15 g (88%) of compound 7 are obtained as a colorless solid. Melting point 177-178° C.; IR (KBr) 3190, 2920, 1700, 1585 cm−1; 1H-NMR (CDCl3) δ 8.50 (sbr, 1H), 8.16 (d, 8.6 Hz, 2H), 8.00 (d, 8.6 Hz, 2H), 7.51 (d, 8.6 Hz, 2H), 7.47 (d, 8.6 Hz, 2H), 3.96 (s, 3H), 3.93 (s, 3H); MS (EI) m/z 313 (M+). Anal. calc. for C17H15NO5: C, 65.17; H, 4.83; N, 4.47. Found C, 65.14; H, 4.78; N, 4.47.

Provenance & Evidence