Ethanol → Ethyl 2-naphthylacetate
Reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.C(O[O:17][C:18]([CH3:21])(C)C)(C)(C)C.[C]=O.[CH2:24]([OH:26])C>>[CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[CH2:1][C:24]([O:17][CH2:18][CH3:21])=[O:26]Participants
Conditions
- Temperature
- 120 °C
Procedure
2-Methylnaphthalene (2.13 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 78 mg ethyl 2-naphthaleneacetate was obtained by column chromatography, in a yield of 73%. 1HNMR (400 MHz, CDCl3) δ 1.24 (t, J=6.8 Hz, 3H), 3.78 (s, 2H), 4.14 (q, J=7.2 Hz, 2H), 7.41-7.49 (m, 3H), 7.73 (s, 1H), 7.79-7.83 (m, 3H); 13CNMR (100 MHz, CDCl3) δ 14.2, 41.6, 60.9, 125.8, 126.1, 127.4, 127.7, 127.9, 128.2, 131.7, 132.5, 133.5, 171.6; HRMS (ESI) calcd. for C14H14NaO2 [M+Na]: 237.0886. found: 237.0886. The ethyl 2-naphthaleneacetate 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, 62 mg product 2-naphthaleneacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 91%.
Workup
- additionwas introduced
Sources & evidence
- ORD record
- ord-f2e8a700e1a445d69248c2382b35fa28
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921591B2
Reaction notes
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