Hydrochloric Acid → HCID 178466058, compound

Participants

Reaction Steps

1,1′-Diacetylferrocene (5.0 g, 20 mmol) in toluene (20 mL) was added to a freshly prepared mixture of zinc/mercury amalgam (3.0 g of granulated Zn, 0.2 g of HgCl2), 10 M HCl (20 mL) and water (20 mL). The reaction mixture was heated to reflux for 4 h with vigorous stirring. The mixture was cooled to rt and extracted with toluene (3×50 mL) and the organic layer was washed with water (3×100 mL) and satd aq NaHCO3 (3×50 mL). The organic layer was dried (MgSO4), evaporated, and chromatographed (silica, petroleum ether:ether, 1:10) to afford 2.8 g (60%) of a red-brown oil. 1H NMR δ 1.13 (t, J=7.5 Hz, 3H), 2.26 (q, J=7.5 Hz, 2H), 2.36 (s, 3H), 4.08 (s, 4H), 4.44 (t, J=2.1 Hz, 2H), 4.69 (t, J=2.1 Hz, 2H); 13C NMR δ 15.4, 22.2, 28.2, 69.8, 69.9, 70.7, 73.6, 92.5, 202.8; FAB-MS obsd 256.0544, calcd exact mass 256.0551 (C14H16FeO). Spectral and physical properties concur with published data (Rosenblum et al. (1958) J. Am. Chem. Soc., 80: 5443-5448).

Provenance & Evidence