Ethanol → Ethyl (4-butoxyphenyl)acetate
Reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].C(O[O:18][C:19]([CH3:22])(C)C)(C)(C)C.[C]=O.[CH2:25]([OH:27])C>>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C:25]([O:18][CH2:19][CH3:22])=[O:27])=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]Participants
Conditions
- Temperature
- 120 °C
Procedure
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%.
Workup
- additionwas introduced
Sources & evidence
- ORD record
- ord-ee081debdaf9480b8511f6be1e2c52fd
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921591B2
Reaction notes
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