Carbon Dioxide → 5-tert-Butyl-4-(2-methoxy-ethoxymethoxy)-2-methyl benzoic acid

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A solution of 1-bromo-5-tert-butyl-4-(2-methoxy-ethoxymethoxy)-2-methyl-benzene from Example ZZ (44.7 g, 135 mmol) in dry THF was cooled to -78° C. under nitrogen and treated with 1.6 M n-butyllithium (93 mL, 149 mmol). The solution was stirred at -78° C. for 45 minutes and then poured over crushed dry ice. The mixture was allowed to warm to room temperature. Et2O (100 mL) and 2N NaOH (200 mL) were added; the organic layer was separated and re-extracted with 2N NaOH. The aqueous layers were combined, acidified to pH 2 with 6N HCl, and extracted with EtOAc. The combined organic extracts were washed with brine, dried (MgSO4), and concentrated to give the title compound. 1H NMR (CDCl3) δ 1.35 (s, 9 H), 2.57 (s, 3 H), 3.37 (s, 3 H), 3.57 (m, 2 H), 3.81 (m, 2 H), 5.35 (s, 2 H), 6.98 (s, 1 H), 8.01 (s, 1 H).

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