Water → Methyl 2-isopropoxy-4-methoxybenzoate

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A solution of 10.0 g (54.9 mmol) methyl 4-methoxysalicylate in 35 ml of dimethyl sulfoxide is treated dropwise with 7.4 g (65.9 mmol) of potassium t-butoxide in 75 ml of dimethylsulfoxide. The resulting pale yellow solution is stirred at 25° C. under nitrogen for 70 minutes. Then 19.7 g (159.8 mmol) of 2-bromopropane is added and the resulting mixture is stirred at 25° C. for 70 hours. The reaction mixture is poured onto 400 ml of H2O and the resulting solution is extracted with diethyl ether (3×125 ml). The combined extracts are washed with aqueous saturated NaCl, dried (Na2SO4) and concentrated in vacuo to give 8.5 g of the crude product as a yellow oil. Flash chromatography (SiO2, 18×65 cm, 15% ethyl acetate-hexane) gives 7.45 g (12.31 g theoretical, 61%) of analytically pure methyl 4-methoxy-2-(1-methylethoxy)benzoate as a colorless oil.

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