Ethanol → Ethyl 3,5-dimethylphenylacetate

Participants

Reaction Conditions

Reaction Steps

Mesitylene (1.8 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 85 mg ethyl 3,5-dimethylphenylacetate was obtained by column chromatography, in a yield of 89%. 1HNMR (400 MHz, CDCl3) δ 1.24 (t, J=7.2 Hz, 3H), 2.30 (s, 6H), 3.53 (s, 2H), 4.12 (q, J=7.2 Hz, 2H), 6.84-6.95 (m, 3H); 13CNMR (100 MHz, CDCl3) δ 14.2, 21.3, 41.3, 60.8, 127.0, 128.7, 133.9, 138.1, 171.9; HRMS (ESI) calcd. for C12H16NaO2 [M+Na]: 215.1043. found: 215.1040. The ethyl 3,5-dimethylphenylacetate 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, 70 mg product 3,5-dimethylphenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 96%.

Provenance & Evidence