Ethanol → Ethyl phenylacetate

HRID 1411196Notes

Reaction equation

HRID 1411196 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC(S(N(S([C:22]2[CH:27]=CC=CC=2)(=O)=O)F)(=O)=O)=CC=1.[C]=[O:29].[CH2:30]([OH:32])C>>[C:1]1([CH2:7][C:30]([O:32][CH2:27][CH3:22])=[O:29])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 1140TolueneHCID 588007N-FluorobenzenesulfonimideHCID 178418416HCID 178418416, compound2×

Product 1

HCID 7590Ethyl phenylacetateYield 37%

Conditions

Temperature
120 °C

Procedure

Toluene (1.38 g), ethanol (46 mg), N-fluorodibenzenesulfonamide (158 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 30 mg ethyl phenylacetate was obtained by column chromatography, in a yield of 37%. 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, 23 mg product phenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 92%.

Workup

  1. additionwas introduced

Sources & evidence

ORD record
ord-d9eeade72695460f9e569c976522e7d2
Source dataset
uspto-grants-2014_12
Patent number
US08921591B2

Reaction notes

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