Pyridine → 4-Nitrobenzyl thioacetate

Participants

Reaction Conditions

Reaction Steps

Thioacetic acid (20 cm3, 0.28 mol) and anhydrous pyridine (15.2 cm3, 0.188 mol) were added to a solution of 4-nitrobenzyl chloride (12.0 g, 70 mmol) in anhydrous tetrahydrofuran (200 cm3). The stirred reactants were heated at 50° C. for 24 h. The cooled products were filtered and the flltrate was evaporated under reduced pressure. The residue was dissolved in dichloromethane (300 cm3) and the resulting solution was washed with saturated aqueous sodium hydrogen carbonate (2×250 cm3), dried (MgSO4) and concentrated under reduced pressure. The residue was crystallized from ethyl acetate--petroleum ether (bp 60°-80° C.) to give 4-nitrobenzyl thioacetate 16a (11.43 g, 77%) as pale yellow needles, m.p. 55.5°-57.5° C.

Provenance & Evidence