Fluorene-1-carboxylic acid → 1-Fluorenemethanol

HRID 1089847

Reaktionsgleichung

Reaktionsgleichung von HRID 1089847
[C:1]1([C:14](O)=[O:15])[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1>C1COCC1>[C:1]1([CH2:14][OH:15])[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Komponenten

3

Edukt 1

HCID 80468Fluorene-1-carboxylic acid

Produkt 1

HCID 523071-FluorenemethanolAusbeute 68,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 1-fluorenecarboxylic acid (10.0 g, 47.6 mmol) in THF (150 mL) at 0° C. was charged With a 1M solution of BH3 -THF complex in THF (80 mL, 80 mmol). The reaction mixture was stored overnight at room temperature then quenched with 30 mL of 10% AcOH in methanol. After dilution with water (100 mL), the water layer was extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with 10% potassium carbonate solution, water, brine, dried over magnesium sulfate and evaporated. The residue (white crystals) was washed with ether and dried to afford 1-fluorenemethanol (6.4 g, 68.5%).

Aufarbeitung

  1. customthen quenched with 30 mL of 10% AcOH in methanol
  2. extractionAfter dilution with water (100 mL), the water layer was extracted with ethyl acetate (3×50 mL)
  3. washThe combined organic extracts were washed with 10% potassium carbonate solution, water, brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. washThe residue (white crystals) was washed with ether
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d4abbb86065b4b868f48615ea64e945e
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05079260

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