2-Methyl-9-fluorenecarboxylic acid → 2-Methyl-9-fluorenemethanol

HRID 1089828

Reaktionsgleichung

Reaktionsgleichung von HRID 1089828
[CH3:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]([C:15](O)=[O:16])[C:4]=2[CH:3]=1>C1COCC1>[CH3:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]([CH2:15][OH:16])[C:4]=2[CH:3]=1

Komponenten

3

Edukt 1

HCID 199784182-Methyl-9-fluorenecarboxylic acid

Produkt 1

HCID 150450582-Methyl-9-fluorenemethanolAusbeute 80,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 2-methyl-9-fluorenecarboxylic acid (6 g, 26.8 mmol) in 300 mL of THF at 0° C. was charged with IM THF solution of BH3-THF complex (53.5 mL, 53.5 mmol). The reaction mixture was stirred overnight then quenched with 30 mL of 10% acetic acid in methanol and diluted with 300 mL of water. The layers were separated, the aqueous phase was extracted with ethyl acetate (3×50 mL), the combined extracts were dried over magnesium sulfate and evaporated to give colorless oil. Crystallization was accomplished upon treatment of the oil with 200 mL of hexane. Recrystallization from ethanol:water 4:1 afforded 4.55 g (80.6%) of 2-methyl-9-fluorenemethanol.

Aufarbeitung

  1. customthen quenched with 30 mL of 10% acetic acid in methanol
  2. additiondiluted with 300 mL of water
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (3×50 mL)
  5. dry with materialthe combined extracts were dried over magnesium sulfate
  6. customevaporated
  7. customto give colorless oil
  8. customCrystallization
  9. customRecrystallization from ethanol:water 4:1

Quellen und Nachweise

ORD-Eintrag
ord-0e55f2c32a4840bb82489d2f96734c46
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05079260

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