Ethanol → HCID 57060897, compound
Reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)[CH2:2][CH3:3].C(O[O:17][C:18]([CH3:21])(C)C)(C)(C)C.[C]=O.[CH2:24]([OH:26])C>>[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C:24]([O:17][CH2:18][CH3:21])=[O:26])=[CH:9][CH:10]=1)[CH2:2][CH3:3]Participants
Conditions
- Temperature
- 120 °C
Procedure
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%.
Workup
- additionwas introduced
Sources & evidence
- ORD record
- ord-d57ac4ebd4e046ddaed1e9aba62d9a0d
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921591B2
Reaction notes
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