Hydrochloric Acid → HCID 13911211, compound

Participants

Reaction Steps

To a stirring solution of p-nitrobenzoyl chloride (76.1 g, 0.410 mol) in 250 mL nitrobenzene were added 82 g of AlCl3 (0.62 mol). To this mixture a solution of 50 grams of 2,6-dimethylphenol (0.41 mole) in 250 mL nitrobenzene was added dropwise over a period of 45 minutes, and the resulting mixture was stirred 16 hours at room temperature. The reaction was poured into 2L of 3% HCl and ice and extracted 3×1L with Et2O (i.e., three times with 1L each time of diethyl ether). The combined ethereal layers were washed with 1L of saturated NaHCO3, then extracted 2×1L with 10% NaOH. The combined basic extracts were acidified with concentrated HCl to give a white precipitate; filtration followed by recrystallization from CH3OH/H2O gave 37 g (33%) of white powder consistent with the desired product by TLC, IR, mass spectroscopy, NMR and elemental analysis, m.p. 182.5-184.5.

Provenance & Evidence