Ethanol → Ethyl 4-methoxyphenylacetate

HRID 1411171Notes

Reaction equation

HRID 1411171 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1.C(O[O:15][C:16]([CH3:19])(C)C)(C)(C)C.[C]=O.[CH2:22]([OH:24])C>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:22]([O:15][CH2:16][CH3:19])=[O:24])=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 77314-MethylanisoleHCID 8033Di-tert-butyl peroxideHCID 178418416HCID 178418416, compound2×

Product 1

HCID 84174Ethyl 4-methoxyphenylacetateYield 85%

Conditions

Temperature
120 °C

Procedure

p-Methoxy toluene (1.83 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 82 mg ethyl p-methoxyphenylacetate was obtained by column chromatography, in a yield of 85%. 1HNMR (400 MHz, CDCl3) δ 1.23 (t, J=6.8 Hz, 3H), 3.54 (s, 2H), 3.79 (s, 3H), 4.11 (q, J=6.8 Hz, 2H), 6.84-6.88 (m, 2H), 7.18-7.22 (m, 2H); 13CNMR (100 MHz, CDCl3) δ 14.2, 40.5, 55.3, 60.8, 113.9, 126.3, 130.3, 158.7, 171.9; HRMS (ESI) calcd. for C11H14NaO3 [M+Na]: 217.0835. found: 217.0838. The ethyl p-methoxyphenylacetate 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, 64 mg product p-methoxyphenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 91%.

Workup

  1. additionwas introduced

Sources & evidence

ORD record
ord-724c6f7db1ab48dba356ec63e8bbd326
Source dataset
uspto-grants-2014_12
Patent number
US08921591B2

Reaction notes

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