Dimethyl Carbonate → 4-Tert-butyl-2-(carboxymethyl)benzoic acid

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Reaction Conditions

Reaction Steps

An amount of 26 mL (198 mmol) of Lithium diiopropylamide (Aldrich) is added to a three neck flask cooled to −40° C. To this is added drops wise, a mixture of 4-tert-butyl-2-methyl-benzoic acid 1.9 g (9.9 mmol) and dimethyl carbonate 3.3 mL (39.6 mmol) in 5 mL of tetrahydrofuran, while keeping the temperature at −60° C. After the addition, the temperature is kept between −40° C. to −60° C. for four hours, then brought to 0° C. and quenched with 25 mL of water. The mixture is allowed to stir at room temperature for two hours and acidify to pH 2 with hydrogen chloride, extracted 3× with ethyl acetate, dried over magnesium sulfate and evaporated.

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