Ethanol → Ethyl phenylacetate

HRID 1411164Notes

Reaction equation

HRID 1411164 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O[O:13][C:14]([CH3:17])(C)C)(C)(C)C.[C]=O.[CH2:20]([OH:22])C>>[C:1]1([CH2:7][C:20]([O:13][CH2:14][CH3:17])=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 1140TolueneHCID 8033Di-tert-butyl peroxideHCID 178418416HCID 178418416, compound2×

Product 1

HCID 7590Ethyl phenylacetateYield 93%

Conditions

Temperature
120 °C

Procedure

Toluene (1.38 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 76 mg ethyl phenylacetate was obtained by column chromatography, in a yield of 93%. 1HNMR (400 MHz, CDCl3) δ 1.23 (t, J=7.2 Hz, 3H), 3.61 (s, 2H), 4.12 (q, J=7.2 Hz, 2H), 7.24-7.35 (m, 5H); 13CNMR (100 MHz, CDCl3) δ 14.2, 41.5, 60.9, 127.0, 128.6, 129.3, 134.2, 171.6; HRMS (ESI) calcd. for C10H12NaO2 [M+Na]: 187.0728. found: 187.0730. The ethyl phenylacetate 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, 59 mg product phenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 93%.

Workup

  1. additionwas introduced

Sources & evidence

ORD record
ord-90466d33a24644f08da6541f14b1c690
Source dataset
uspto-grants-2014_12
Patent number
US08921591B2

Reaction notes

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