Ethanol → Ethyl (2-methylphenyl)acetate
Reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=1[CH3:8].C(O[O:14][C:15]([CH3:18])(C)C)(C)(C)C.[C]=O.[CH2:21]([OH:23])C>>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=1[CH2:8][C:21]([O:14][CH2:15][CH3:18])=[O:23]Participants
Conditions
- Temperature
- 120 °C
Procedure
o-Xylene (1.59 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 81 mg ethyl o-methylphenylacetate was obtained by column chromatography, in a yield of 91%. 1HNMR (400 MHz, CDCl3) δ 1.23 (t, J=7.2 Hz, 3H), 2.32 (s, 3H), 3.63 (s, 2H), 4.12 (q, J=7.2 Hz, 2H), 7.15-7.21 (m, 4H); 13CNMR (100 MHz, CDCl3) δ 14.2, 19.6, 39.3, 60.8, 126.1, 127.3, 130.1, 130.3, 132.9, 136.8, 171.5; HRMS (ESI) calcd. for C11H14NaO2 [M+Na]: 201.0886. found: 201.0882. The ethyl o-methylphenylacetate 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, 66 mg product o-methylphenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 97%.
Workup
- additionwas introduced
Sources & evidence
- ORD record
- ord-92c7e86a9cb144dbbd30a6e18ff2e64a
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921591B2
Reaction notes
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