HCID 59556611, compound → 4-[2-(Tert-butoxy)-2-oxoethoxy]benzoic acid

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Reaction Steps

A 500 mL high-pressure flask was charged with benzyl 4-(2-tert-butoxy-2-oxoethoxy)benzoate (2.06 g, 6.02 mmol) in methanol (100 ml). Palladium on carbon (0.320 g, 0.301 mmol) was added, the resulting suspension was allowed to shake under an atmosphere of hydrogen (47 Psi) at room temperature for 6 h. The mixture was filtered through Celite®), the colorless filtrate was concentrated to afford 4-(2-tert-butoxy-2-oxoethoxy)benzoic acid (1.5 g, 5.95 mmol, 99% yield) as pale yellow solid. LC/MS (Table 1, Method a) Rt=3.03 min.; MS m/z: 251.30 (M−H)−. 1H NMR (400 MHz, Solvent d-DMSO) ppm 7.88 (d, J=8.99 Hz, 2H), 6.98 (d, J=9.00 Hz, 2H), 4.75 (s, 2H), 1.43 (s, 9H).

Provenance & Evidence