Ethanol → Ethyl (4-butoxyphenyl)acetate

Participants

Reaction Conditions

Reaction Steps

4-n-butoxytoluene (2.46 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 107 mg ethyl 2-(4-n-butoxyphenyl)acetate was obtained by column chromatography, in a yield of 91%. 1HNMR (400 MHz, CDCl3) δ 0.95 (t, J=7.6 Hz, 3H), 1.23 (t, J=7.2 Hz, 3H), 1.45-1.53 (m, 2H), 1.72-1.79 (m, 2H), 3.54 (s, 2H), 3.92 (t, J=6.4 Hz, 2H), 4.11 (q, J=7.2 Hz, 2H), 6.83-6.86 (m, 2H), 7.17-7.19 (m, 2H); 13CNMR (100 MHz, CDCl3) δ 13.9, 14.2, 19.3, 31.3, 40.6, 60.8, 67.7, 114.6, 126.0, 130.2, 158.3, 171.9; HRMS (ESI) calcd. for C14H20NaO3 [M+Na]: 259.1305. found: 259.1312. The ethyl 2-(4-n-butoxyphenyl)acetate 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, 91 mg product 2-(4-n-butoxyphenyl)acetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 96%.

Provenance & Evidence