Water → 1-Pyrenemethanol

HRID 1654609

Reaktionsgleichung

Reaktionsgleichung von HRID 1654609
[C:1]1([CH:17]=[O:18])[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.[BH4-].[Na+].O>C(O)C>[OH:18][CH2:17][C:1]1[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 2328481-PyrenecarboxaldehydeHCID 4311764Sodium borohydride

Produkt 1

HCID 1049771-Pyrenemethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a suspension of pyrene carboxaldehyde (9.6 g, 42 mmol) in ethanol (50 mL) was added NaBH4 (2 g) and the mixture was stirred at room temperature for 6 hours. Water (100 mL) was added and the mixture was extracted with ether (2×50 mL). The organic layer was dried over MgSO4, and the solvent evaporated under reduced pressure to give a light-yellow solid which was recrystallized from ethyl acetate to afford prisms, m.p. 125°-126° C., yield: 8.3 g, 86%.

Aufarbeitung

  1. extractionthe mixture was extracted with ether (2×50 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. customthe solvent evaporated under reduced pressure
  4. customto give a light-yellow solid which
  5. customwas recrystallized from ethyl acetate
  6. customto afford prisms, m.p. 125°-126° C., yield: 8.3 g, 86%

Quellen und Nachweise

ORD-Eintrag
ord-a1acb7d8ba444f7094c90d74693ec7d5
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05409666

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