Water → (4-Cyclopropylphenyl)methanol

HRID 7360

Reaktionsgleichung

Reaktionsgleichung von HRID 7360
[CH:1]1([C:4]2[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[BH4-].[Li+].O>CO>[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([CH2:8][OH:9])=[CH:10][CH:11]=2)[CH2:2][CH2:3]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 115064744-Cyclopropylbenzaldehyde

Produkt 1

HCID 22135711(4-Cyclopropylphenyl)methanolAusbeute 95,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 4-cyclopropylbenzaldehyde (0.71 g) in methanol (10 mL) was added lithium borohydride (2 mol/L tetrahydrofuran solution, 3.7 mL), and the mixture was warmed to room temperature and stirred for 30 minutes. To the reaction mixture was added water, and the mixture was extracted with diethyl ether. The organic layer was washed with 1 mol/L hydrochloric acid solution and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1) to give 4-cyclopropylbenzyl alcohol (0.69 g).

Aufarbeitung

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe organic layer was washed with 1 mol/L hydrochloric acid solution and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-621039449c2a4a8292dc2cf8bcf28ed2
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087579B2

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