Hydrochloric Acid → HCID 15398356, compound

Participants

Reaction Conditions

Reaction Steps

4-Aminobenzyl alcohol (3.0 g, 24 mmol) was suspended in a mixture of conc. HCl (20 mL) and H2O (20 mL) and cooled to 0° C. under stirring. A solution of NaNO2 (2.1 g, 30 mmol) in H2O (10 mL) was added dropwise while the temperature was carefully maintained between 0–5° C. The resulting mixture was stirred for 30 min at 0° C., then slowly added at 0° C. to a solution of ferrocene (3.7 g, 20 mmol) in toluene (100 mL), resulting in gas evolution. After complete addition, the reaction mixture was stirred at 0° C. for 6 h and warmed to rt. Stirring was continued for another 6 h. The layers were separated and the aqueous layer was extracted with toluene (3×100 mL). The combined organic layers were washed with satd aq NaHCO3 (3×100 mL), brine (3×100 mL), dried (MgSO4) and filtered. The solvent was removed under reduced pressure and the resulting residue was purified by column chromatography (silica, petroleum ether/diethyl ether, 10:2) to afford 0.94 g (20%) of 4-ferrocenylbenzyl alcohol 16 (as well as 2.1 g (45%) of 4-ferrocenylbenzaldehyde 17).

Provenance & Evidence