Ethanol → alpha-Naphthaleneacetic acid, ethyl ester

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1-Methylnaphthalene (2.13 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 89 mg ethyl 1-naphthaleneacetate was obtained by column chromatography, in a yield of 83%. 1HNMR (400 MHz, CDCl3) δ 1.20 (t, J=7.2 Hz, 3H), 4.06 (s, 2H), 4.12 (q, J=7.2 Hz, 2H), 7.39-7.55 (m, 4H), 7.78-7.80 (m, 1H), 7.84-7.85 (m, 1H), 7.99-8.01 (m, 1H); 13CNMR (100 MHz, CDCl3) δ 14.2, 39.3, 60.9, 123.9, 125.5, 125.8, 126.3, 127.9, 128.0, 128.7, 130.7, 132.2, 133.9, 171.6; HRMS (ESI) calcd. for C14H14NaO2 [M+Na]: 237.0886. found: 237.0889. The ethyl 1-naphthaleneacetate 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, 71 mg product 1-naphthaleneacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 92%.

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