Acetone → 2-Ethyl-1-hydroxy-4-phenylindan

HRID 1489314

Reaktionsgleichung

Reaktionsgleichung von HRID 1489314
B.[Na].[CH2:3]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:6]1=[O:20])[CH3:4].CC(C)=O>C(O)C>[CH2:3]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]1[OH:20])[CH3:4]

Komponenten

5

Edukt 3

HCID 180AcetoneHCID 221732182-Ethyl-4-phenyl-1-indanoneHCID 178418435HCID 178418435, Verbindung2×

Produkt 1

HCID 223402152-Ethyl-1-hydroxy-4-phenylindanAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To a 200-ml three-necked round flask (equipped with stirrer chip, Dimroth condenser, dropping funnel and thermometer) were introduced 0.85 g (22.6 mmol) of sodium boron hydride and 28 ml of ethanol. In a nitrogen atmosphere at room temperature, to the flask was dropwise added a solution obtained by dissolving 10.6 g (45.1 mmol) of the 2-ethyl-4-phenyl-l-indanone obtained above in 20 ml of ethanol. After the dropping was completed, the temperature of the system was elevated to 50° C. so as to further perform reaction for 3.5 hours. After the reaction, the system was cooled, and acetone was dropwise added to decompose the unreacted sodium boron hydride. Then, the reaction mixture was concentrated under reduced pressure and extracted with 50 ml of water and 50 ml of ether. The organic phase was separated, and the aqueous phase was extracted twice with 50 ml of ether, followed by mixing the organic phases together. The whole organic phase was washed with 100 ml of a saturated saline solution and dried with anhydrous Na2SO4. Then, the solvent was distilled off under reduced pressure to obtain 10.67 g of the aimed product (mixture of two kinds of isomers) as a viscous light yellow liquid (yield: 99%). The properties of the product thus obtained are described below.

Aufarbeitung

  1. customTo a 200-ml three-necked round flask (equipped with stirrer chip, Dimroth condenser, dropping funnel and thermometer)
  2. additionIn a nitrogen atmosphere at room temperature, to the flask was dropwise added a solution
  3. customobtained
  4. customthe temperature of the system was elevated to 50° C. so as to further perform reaction for 3.5 hours
  5. customAfter the reaction
  6. temperaturethe system was cooled
  7. concentrationThen, the reaction mixture was concentrated under reduced pressure
  8. extractionextracted with 50 ml of water and 50 ml of ether
  9. customThe organic phase was separated
  10. extractionthe aqueous phase was extracted twice with 50 ml of ether
  11. additionby mixing the organic phases together
  12. washThe whole organic phase was washed with 100 ml of a saturated saline solution
  13. dry with materialdried with anhydrous Na2SO4
  14. distillationThen, the solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3f963f8768fe458ba36f8762e57ad203
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05677408

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