Sodium Sulfite → 4-[2-Ethoxy-2-(2,2,2-trichloro-ethoxy carbonyl)-ethyl]-benzoic acid

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Reaction Steps

2-Ethoxy-3-(4-hydroxymethyl-phenyl)-propionic acid 2,2,2-trichloroethyl ester (0.044 g, 0.125 mmol) was dissolved in acetone (3 mL) and KMnO4 (0.039 g, 0.247 mmol) was added and the purple solution was stirred for 4 h at room temperature. Saturated aq. Na2SO3 solution was added and after 2 min. stirring, the mixture was diluted with EtOAc and aq. HCl (2N) resulting in two clear and colorless phases. The organic layer was separated and dried (MgSO4) and evaporated to afford the desired carboxylic acid which was proceeded on to the next step without further purification (0.034 g, 75%). 1H NMR (400 MHz, CDCl3): δ 8.01-8.03 (d, 2H), 7.36-7.38 (d, 2H), 4.73-4.83 (q, 2H), 4.15-4.18 (m, 1H), 3.65-3.69 (m, 1H), 3.33-3.37 (m, 1H), 3-07-3.20 (m, 2H), 1.14 (t, 3H).

Provenance & Evidence