Ethanol → HCID 57060897, compound

Participants

Reaction Conditions

Reaction Steps

4-n-propoxytoluene (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 88 mg ethyl 2-(4-n-propoxyphenyl)acetate was obtained by column chromatography, in a yield of 79%. 1HNMR (400 MHz, CDCl3) δ 1.00 (t, J=7.6 Hz, 3H), 1.23 (t, J=7.2 Hz, 3H), 1.75-1.84 (m, 2H), 3.54 (s, 2H), 3.88 (t, J=6.4 Hz, 2H), 4.11 (q, J=7.2 Hz, 2H), 6.83-6.87 (m, 2H), 7.16-7.20 (m, 2H); 13CNMR (100 MHz, CDCl3) δ 10.5, 14.2, 22.6, 40.6, 60.8, 69.5, 114.6, 126.0, 130.2, 158.2, 171.9; HRMS (ESI) calcd. for C13H18NaO3 [M+Na]: 245.1148. found: 245.1157. The ethyl 2-(4-n-propoxyphenyl)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, 73 mg product 2-(4-n-propoxyphenyl)acetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 95%.

Provenance & Evidence