Ethanol → Ethyl phenylacetate

Participants

Reaction Conditions

Reaction Steps

Toluene (1.38 g), ethanol (46 mg), di-tert-butyl peroxide (73 mg, 1 equivalent), and Pd(Xantphos)Cl2 (3.8 mg, 1 mol %) were added into a reaction kettle, into which 10 atm carbon monoxide was introduced. The reaction was heated to 120° C., and stirred at this constant temperature for 16 h. After the reaction was completed, carbon monoxide was discharged, and 76 mg ethyl phenylacetate was obtained by column chromatography, in a yield of 93%. 1HNMR (400 MHz, CDCl3) δ 1.23 (t, J=7.2 Hz, 3H), 3.61 (s, 2H), 4.12 (q, J=7.2 Hz, 2H), 7.24-7.35 (m, 5H); 13CNMR (100 MHz, CDCl3) δ 14.2, 41.5, 60.9, 127.0, 128.6, 129.3, 134.2, 171.6; HRMS (ESI) calcd. for C10H12NaO2 [M+Na]: 187.0728. found: 187.0730. The ethyl phenylacetate obtained was dissolved in 1,4-dioxane. 6 N sodium hydroxide solution was added, and the reaction was heated to 60° C. After 2 h of reaction, the pH value was adjusted to 1 by adding 2 N hydrochloric acid. After removing the organic solvent under reduced pressure, 59 mg product phenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 93%.

Provenance & Evidence