Methanol → 1-Methoxy-2,2,6,6-tetramethylpiperidin-4-yl 3,5-Di-t-butyl-4-hydroxybenzoate

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Reaction Steps

A solution of 7.6 g (28.3 mmol) of 3,5-di-t-butyl-4-hydroxybenzoyl chloride in toluene (35 ml) is added dropwise over 20 minutes to a solution of 5.3 g (28.3 mmol) of 4-hydroxy-1-methoxy-2,2,6,6-tetramethylpiperidine and 2.46 g (31.1 mmol) of pyridine in toluene (30 ml). The reaction temperature is kept below 60° C. during the addition and the reaction mixture is stirred for one hour at 55°-60° C. after the addition and then filtered. The filtrate is washed with 1N HCl (2×50 ml), water (100 ml), saturated NaHCO3 (100 ml), dried (magnesium sulfate), and concentrated. The crude oil is chromatographed on silica gel (9:1 hexane:ethyl acetate) to obtain 7.3 g (61% yield of a white crystalline solid, m.p. 126°-8° C. (methanol).

Provenance & Evidence