4-Benzyloxy-3-ethyl-5-methyl-benzoic acid tert-butyl ester → 3-Ethyl-4-hydroxy-5-methyl-benzoic acid tert-butyl ester

Participants

Reaction Steps

To a solution of 4-benzyloxy-3-ethyl-5-methyl-benzoic acid tert-butyl ester (9.02 g, 27.6 mmol) in THF (50 mL) and ethanol (50 mL), Pd/C (400 mg, 10% Pd) is added. The slurry is stirred at rt for 24 h under 1 bar of H2. The catalyst is removed by filtration and the filtrate is concentrated, dissolved again in THF (50 mL) and ethanol (50 mL), and again treated with Pd/C (400 mg, 10% Pd). The slurry is stirred at rt for 24 h under 1 bar of H2. The catalyst is again removed by filtration and the filtrate is concentrated and dried to give 3-ethyl-4-hydroxy-5-methyl-benzoic acid tert-butyl ester as a pale yellow oil (7.13 g). LC-MS: tR=1.01 min; 1H NMR (CDCl3): δ 1.28 (t, J=7.8 Hz, 3H), 1.61 (s, 9H), 2.30 (s, 3H), 2.67 (q, J=7.5 Hz, 2H), 5.13 (br s, 1H), 7.67 (s, 1H), 7.69 (s, 1H).

Provenance & Evidence