Hydrochloric Acid → 4-Chloro-3-nitrophenyl 3,5-di-t-butyl-4-hydroxybenzoate

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Reaction Steps

3,5-Di-t-butyl-4-hydroxybenzoyl chloride (56.2 g; 0.209 mole) in tetrahydrofuran (70 ml) was added with stirring to a solution of 4-chloro-3-nitrophenol (36.3 g; 0.209 mole) in pyridine (170 ml) at 0° C. over 20 minutes. The reaction mixture was stirred at room temperature for 22 hours and poured into an ice cold solution of 10M-hydrochloric acid (350 ml) and water (1400 ml). The mixture was extracted into ether (500 ml) and the ethereal extract washed successively with 2M-hydrochloric acid (150 ml), 2% sodium carbonate solution (4×150 ml) and water (2×100 ml). The extract was dried and the ether removed to give a dark orange oil (90 g). This material was chromatographed (silica) eluting with 4:1 hexane:ethyl acetate, to give the product (60.6 g; 72%) as a yellow viscous oil.

Provenance & Evidence