Water → 1,5-Diphenylpentane-1,5-diol

HRID 132743

Reaktionsgleichung

Reaktionsgleichung von HRID 132743
[C:1]1([C:7](=[O:19])[CH2:8][CH2:9][CH2:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O1CCCC1.O>C(OCC)(=O)C>[C:13]1([CH:11]([OH:12])[CH2:10][CH2:9][CH2:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[OH:19])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 804321,3-DibenzoylpropaneHCID 21226445Aluminium lithium hydride2×

Produkt 1

HCID 2261681,5-Diphenylpentane-1,5-diolAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

While cooled by an ice-bath and stirred intensely, 0.0 mol 1,5-diphenyl-1,5-pentandione was added dropwise slowly to a mixture of 3 g LiAlH4 and 100 ml anhydrous tetrahydrofuran. The mixture was heated refluxing for 5 hours, then cooled. Excess LiAlH4 was decomposed with water. After mixing completely the reaction mixture with ethyl acetate, the mixture was filtered, and the filtrate was dried over anhydrous sodium sulfate. The solvent was removed. Column chromatography gave 1,5-diphenyl-1,5-pentanediol as a white solid, and the yield was 85%. mp: 64-67° C. IR spectrum had a strong —OH absorption peak at 3400 cm−1, and had no —CO— absorption peak at about 1700 cm−1. This demonstrated that the reduction reaction was carried out completely.

Aufarbeitung

  1. temperatureWhile cooled by an ice-bath
  2. temperatureThe mixture was heated
  3. temperaturerefluxing for 5 hours
  4. temperaturecooled
  5. filtrationthe mixture was filtered
  6. dry with materialthe filtrate was dried over anhydrous sodium sulfate
  7. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-571f1e2567434e34a1dd1f0803be349d
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07388061B2

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