Ethanol → HCID 19797927, compound
Reaction equation
[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(O[O:20][C:21]([CH3:24])(C)C)(C)(C)C.[C]=O.[CH2:27]([OH:29])C>>[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:27]([O:20][CH2:21][CH3:24])=[O:29])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]Participants
Conditions
- Temperature
- 120 °C
Procedure
4-(n-hexyloxy)toluene (2.88 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 116 mg ethyl 2-(4-(n-hexyloxy)phenyl)acetate was obtained by column chromatography, in a yield of 88%. 1HNMR (400 MHz, CDCl3) δ 0.88 (t, J=7.2 Hz, 3H), 1.23 (t, J=7.2 Hz, 3H), 1.31-1.36 (m, 4H), 1.41-1.46 (m, 2H), 1.73-1.79 (m, 2H), 3.54 (s, 2H), 3.91 (t, J=6.8 Hz, 2H), 4.11 (q, J=7.2 Hz, 2H), 6.83-6.87 (m, 2H), 7.17-7.19 (m, 2H); 13CNMR (100 MHz, CDCl3) δ 14.0, 14.2, 22.6, 25.7, 29.3, 25.7, 29.3, 31.6, 40.6, 60.8, 68.0, 114.6, 126.0, 130.2, 158.2, 171.9; HRMS (ESI) calcd. for C16H24NaO3 [M+Na]: 287.1618. found: 287.1622. The ethyl 2-(4-(n-hexyloxy)phenyl)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, 97 mg product 2-(4-(n-hexyloxy)phenyl)acetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 94%.
Workup
- additionwas introduced
Sources & evidence
- ORD record
- ord-9679c60790dc4aabacbbef8ab780dbff
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921591B2
Reaction notes
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