4-Phenylcyclohexanone → HCID 178521548, Verbindung

HRID 715563

Reaktionsgleichung

Reaktionsgleichung von HRID 715563
[C:1]1([CH:7]2[CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[C:1]1([C@H:7]2[CH2:8][CH2:9][C@H:10]([OH:13])[CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 786054-PhenylcyclohexanoneHCID 4311764Sodium borohydride

Produkt 1

HCID 178521548HCID 178521548, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4-Phenylcyclohexanone (4 g) is dissolved under argon in MeOH (25 mL), cooled to 0° C. and treated portionwise with NaBH4 (900 mg). The mixture is stirred for 12 hours while warming to room temperature. The mixture is concentrated and then treated dropwise with water (10 mL). Then concentrated hydrochloric acid (8 mL) is added dropwise. The mixture is extracted with ethylacetate and the organic phase is washed with brine and dried (Na2SO4). The solvents are evaporated and the residue is crystallized from cyclohexane to give the title compound. TLC: rf=0.52 (silicagel, dichloromethane/ethanol 19:1).

Aufarbeitung

  1. temperaturewhile warming to room temperature
  2. concentrationThe mixture is concentrated
  3. additiontreated dropwise with water (10 mL)
  4. additionThen concentrated hydrochloric acid (8 mL) is added dropwise
  5. extractionThe mixture is extracted with ethylacetate
  6. washthe organic phase is washed with brine
  7. dry with materialdried (Na2SO4)
  8. customThe solvents are evaporated
  9. customthe residue is crystallized from cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-9d9563f3f3a34bc8896e1af91df73b00
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187477B2

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