Sodium Hydroxide → 3-(Benzyloxy)-2,2-dimethylpropanoic acid

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Reaction Steps

Adapting procedures or variations thereof according to Rega et al., Eur. J. Org. Chem. 2007, 6, 934-942; Woo et al., J. Org. Chem. 2004, 69(25), 8984-8986; and Abiko et al., Tetrahedron Lett 1986, 27(38), 4537-40, 3.4 mL of an ten molar (10 M) aqueous solution of sodium hydroxide (NaOH) (34.0 mmol) was added to a solution of 3.7 g (16.9 mmol) of methyl-2,2-dimethyl-3-(phenylmethoxy)propanoate (26a) in a mixture of 15 mL of tetrahydrofuran (THF) and 5 mL of methanol (MeOH). The solution was vigorously stirred overnight at room temperature. Upon completion of the reaction, the reaction mixture was further diluted with one molar (1.0 M) hydrochloric acid (HCl) and ethyl acetate (EtOAc) and the phases were separated. The aqueous phase was extracted two additional times with ethyl acetate (EtOAc) and the combined organic extracts were washed with brine. The organic solution was dried over anhydrous magnesium sulfate (MgSO4), filtered, and the solvents and benzyl alcohol were removed under reduced pressure using a rotary evaporator. The crude material was used in the next step without further purification. Three-point-three (3.3) g (93% yield) of the title compound (26b) was obtained as a colorless solid. 1H NMR (400 MHz, CDCl3): δ=1.10 (s, 6H), 3.40 (s, 2H), 4.47 (s, 2H), 7.26-7.35 (m, 5H) ppm. The analytical data was consistent with the proposed structure.

Provenance & Evidence