Pyridine → 4-Hydroxycyclohexyl benzoate

HRID 1718955

Reaktionsgleichung

Reaktionsgleichung von HRID 1718955
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]1(O)([OH:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.N1C=CC=CC=1.[O:24]1CCCC1>>[C:1]([O:8][CH:13]1[CH2:14][CH2:15][CH:10]([OH:16])[CH2:11][CH2:12]1)(=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 8028TetrahydrofuranHCID 19352763Cyclohexane-1,1-diol

Produkt 1

HCID 2381094-Hydroxycyclohexyl benzoateAusbeute 86 %

Versuchsvorschrift

A mixture of benzoyl chloride (50 mL), cyclohexanediol (150 g), pyridine (105 mL) and tetrahydrofuran (1300 mL) was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, the residue was diluted with ethyl acetate, successively washed with saturated aqueous sodium hydrogen carbonate, water, and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as a colorless oil (81.5 g, 86%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washsuccessively washed with saturated aqueous sodium hydrogen carbonate, water, and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-29f4e48b7ce14b9c9b02d5bb20cce98f
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803940B2

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