Ethanol → Ethyl phenylacetate

HRID 1411191

Reaktionsgleichung

Reaktionsgleichung von HRID 1411191
[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>CC(CC(C)=O)=O.CC(CC(C)=O)=O.CC(CC(C)=O)=O.[Co].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[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

Komponenten

7

Edukt 4

HCID 702EthanolHCID 1140TolueneHCID 8033Di-tert-butyl peroxideHCID 178418416HCID 178418416, Verbindung2×

Produkt 1

HCID 7590Ethyl phenylacetateAusbeute 17,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 407384Cobalt(3+) acetylacetonateKatalysatorHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)Katalysator

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Toluene (1.38 g), ethanol (46 mg), di-tert-butyl peroxide (73 mg, 1 equivalent), cobalt acetylacetonate (1.3 mg, 1 mol %), and Xantphos (2.9 mg) 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 14 mg ethyl phenylacetate was obtained by column chromatography, in a yield of 17%. 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, 10 mg product phenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 93%.

Aufarbeitung

  1. additionwas introduced

Quellen und Nachweise

ORD-Eintrag
ord-fc1cf4a8ca97498da9e93ee58aa98354
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921591B2

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