Potassium Bromide → Benzoic acid, 4,4'-carbonylbis-, dimethyl ester

Participants

Reaction Steps

(Kirste, B.; Grimm, M.; Kurreck, H. J. Am. Chem. Soc. 1989, 111, 108-114.) To a suspension of PCC (3.10 g, 14.4 mmol) in anhydrous CH2Cl2 (25 ml) at RT, a solution of the benzyl alcohol 5 (2.70 g, 8.99 mmol) is added slowly dropwise into anhydrous CH2Cl2 (10 ml), and the preparation is stirred at this temperature over night. Subsequently, the mixture is filtered through a small amount of silica gel (CH2Cl2 as eluent). Following the distillation of the solvent, 2.44 g (91%) of compound 6 could be isolated in form of a colorless solid. Melting point 228-230° C. (Kirste et al. 1989, see above, 229.5-230° C.); IR (KBr) 1705, 1630 cm−1; 1H-NMR (CDCl3) δ 8.17 (d, 8.4 Hz, 4H), 7.85 (d, 8.4 Hz, 4H), 3.98 (s, 6H); MS (EI) m/z 298 (M+). Anal. calc. for C17H14O5: C, 68.45; H, 4.73. Found C, 68.30; H, 4.69.

Provenance & Evidence