Ethanol → Ethyl 4-ethoxyphenylacetate
Reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1)[CH3:2].C(O[O:16][C:17]([CH3:20])(C)C)(C)(C)C.[C]=O.[CH2:23]([OH:25])C>>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:23]([O:16][CH2:17][CH3:20])=[O:25])=[CH:6][CH:5]=1)[CH3:2]Participants
Conditions
- Temperature
- 120 °C
Procedure
p-Ethoxy toluene (2.04 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 p-ethoxyphenylacetate was obtained by column chromatography, in a yield of 86%. 1HNMR (400 MHz, CDCl3) δ 1.22 (t, J=7.2 Hz, 3H), 1.38 (t, J=7.2 Hz, 3H), 3.54 (s, 2H), 3.98 (q, J=7.2 Hz, 2H), 4.11 (q, J=6.8 Hz, 2H), 6.83-6.86 (m, 2H), 7.17-7.20 (m, 2H); 13CNMR (100 MHz, CDCl3) δ 13.2, 13.8, 39.5, 59.7, 69.7, 62.4, 113.5, 125.1, 129.2, 156.9, 170.9; HRMS (ESI) calcd. for C12H16NaO3 [M+Na]: 231.0992. found: 231.0989. The ethyl p-ethoxyphenylacetate 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, 72 mg product p-ethoxyphenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 93%.
Workup
- additionwas introduced
Sources & evidence
- ORD record
- ord-2840c7fa0d074777914b8d3fbf8ddb3a
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921591B2
Reaction notes
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