4-Phenyl-2,3-dihydro-1h-inden-1-one → 4-Phenyl-2,3-dihydro-1H-inden-1-ol

HRID 444240Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 444240
[C:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH2:9][CH2:10][C:11]3=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)C.O>[C:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH2:9][CH2:10][CH:11]3[OH:16])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 2

HCID 2633814-Phenyl-2,3-dihydro-1h-inden-1-oneHCID 4311764Sodium borohydride

Produkt 1

HCID 129423854-Phenyl-2,3-dihydro-1H-inden-1-olAusbeute 82,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of 20.8 g (0.10 mole) of 4-phenyl-1-indanone in 150 ml of ethanol was added portionwise 2.0 g (0.06 mole) of sodium borohydride. During the addition the reaction temperature rose to 33° C. Upon complete addition the reaction mixture was allowed to cool to ambient temperature and was stirred for 16 hours. The reaction mixture was mixed in water and concentrated under reduced pressure. A precipitate, which developed during concentration of the aqueous solution, was collected, dried, then recrystallized from toluene-hexane to give 17.3 g of 4-phenyl-1-indanol; m.p. 80.5°-81.5° C. The nmr spectrum was consistent with the proposed structure.

Aufarbeitung

  1. additionDuring the addition the reaction temperature
  2. customrose to 33° C
  3. additionUpon complete addition the reaction mixture
  4. concentrationconcentrated under reduced pressure
  5. customwas collected
  6. customdried
  7. customrecrystallized from toluene-hexane

Quellen und Nachweise

ORD-Eintrag
ord-aa69d333281646eebda2158e34764681
Quelldatensatz
uspto-grants-1981_04
Patentnummer
US04263319

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