Sodium borohydride → 1-Phenylcyclohexanemethanol

HRID 2169288

Reaktionsgleichung

Reaktionsgleichung von HRID 2169288
[C:1]1([C:7]2([CH:13]=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[C:1]1([C:7]2([CH2:13][OH:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 149226061-Phenylcyclohexane-1-carbaldehyde

Produkt 1

HCID 1985171-PhenylcyclohexanemethanolAusbeute 91,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-phenyl-cyclohexanecarbaldehyde (250) (16.4 g, 87.1 mmol) in methanol (200.0 mL) was added NaBH4 (6.62 g, 174.2 mmol) portion-wise at 0° C. The reaction mixture was then stirred at room temperature for 2 h. After completion of the reaction, the solvent was concentrated and the crude product was extracted with ethyl acetate. The organic layer was then washed with water and brine and dried over sodium sulfate and concentrated under reduced pressure to get (1-phenyl-cyclohexyl)-methanol (251) (15.2 g, 91.7%) as a white solid which was sufficiently pure to be used for the next step.

Aufarbeitung

  1. customAfter completion of the reaction
  2. concentrationthe solvent was concentrated
  3. extractionthe crude product was extracted with ethyl acetate
  4. washThe organic layer was then washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-66f33b7649ef455c9f5dea3a4d18ecd7
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045486B2

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