Hydrochloric Acid → 4-(cis-4-Hydroxycyclohexyl)phenol

HRID 2220002Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2220002
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO>[OH:14][CH:11]1[CH2:10][CH2:9][CH:8]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=2)[CH2:13][CH2:12]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 45989164-(4'-Hydroxyphenyl)cyclohexanone

Produkt 1

HCID 101764984-(cis-4-Hydroxycyclohexyl)phenolAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

10 g (0.052 mol) of 4-(4-Hydroxy-phenyl)-cyclohexanone is dissolved in 300 mL of methanol. 2.13 g (0.058 mol) of NaBH4 is added at room temperature by small portion for 2 hours. After stirring over night, the mixture is cooled using an ice-water bath, then hydrolysed with a solution of 10% HCl aqueous solution. The solution is extracted several times with ethyl acetate. The resulting organic phase is washed with water, dried over magnesium sulfate, then concentrated under reduced pressure. The residue recrystallised from ethanol gives pure white crystals (8.7 g, 87% yield).

Aufarbeitung

  1. temperaturethe mixture is cooled
  2. extractionThe solution is extracted several times with ethyl acetate
  3. washThe resulting organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue recrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-d92ced5a02524aa68a92a454c1c763b7
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07416682B2

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