Ethanol → Ethyl m-tolylacetate

HRID 1411169Notes

Reaction equation

HRID 1411169 reaction equation
[C:1]1([CH3:8])[CH:6]=[CH:5][CH:4]=[C:3]([CH3:7])[CH:2]=1.C(O[O:14][C:15]([CH3:18])(C)C)(C)(C)C.[C]=O.[CH2:21]([OH:23])C>>[CH3:8][C:1]1[CH:2]=[C:3]([CH2:7][C:21]([O:14][CH2:15][CH3:18])=[O:23])[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 7929M-XyleneHCID 8033Di-tert-butyl peroxideHCID 178418416HCID 178418416, compound2×

Product 1

HCID 96574Ethyl m-tolylacetateYield 90%

Conditions

Temperature
120 °C

Procedure

m-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 80 mg ethyl m-methylphenylacetate was obtained by column chromatography, in a yield of 90%. 1HNMR (400 MHz, CDCl3) δ 1.23 (t, J=7.2 Hz, 3H), 2.33 (s, 3H), 3.57 (s, 2H), 4.12 (q, J=7.2 Hz, 2H), 7.06-7.09 (m, 3H), 7.19-7.24 (m, 3H); 13CNMR (100 MHz, CDCl3) δ14.2, 21.4, 41.4, 60.8, 126.3, 127.8, 128.5, 130.0, 134.1, 138.2, 171.8; HRMS (ESI) calcd. for C11H14NaO2 [M+Na]: 201.0886. found: 201.0887. The ethyl m-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, 63 mg product m-methylphenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 93%.

Workup

  1. additionwas introduced

Sources & evidence

ORD record
ord-26e594ad622b42fbb44e7b9f38c5fa83
Source dataset
uspto-grants-2014_12
Patent number
US08921591B2

Reaction notes

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