Pyridine → Benzoic acid, acetylmethyl ester

HRID 1645525

Reaktionsgleichung

Reaktionsgleichung von HRID 1645525
N1C=CC=CC=1.C1COCC1.[OH:12][CH2:13][C:14](=[O:16])[CH3:15].[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(OCC)(=O)C>[C:17]([O:12][CH2:13][C:14](=[O:16])[CH3:15])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 8028TetrahydrofuranHCID 8299Hydroxyacetone

Produkt 1

HCID 23137Benzoic acid, acetylmethyl esterAusbeute 87,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a pyridine (25 ml) and THF (10 ml) solution of hydroxyacetone (5 g, 67.5 mmol), benzoyl chloride (12 ml, 103 mmol) was added dropwise at 0° C. in a nitrogen atmosphere and the mixture was stirred for 43 hours at room temperature. Ice was added to the reaction mixture, which was then diluted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, water, and a saline solution, dried over anhydrous sodium sulfate, and concentrated. The obtained crude product was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate=1/0-1/1 gradient). Desired fractions were concentrated to obtain the title compound (10.56 g, 87.8% yield) as a light yellow oil.

Aufarbeitung

  1. additionIce was added to the reaction mixture, which
  2. washThe organic layer was washed with 1N hydrochloric acid, water
  3. dry with materiala saline solution, dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe obtained crude product
  6. customwas purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate=1/0-1/1 gradient)
  7. concentrationDesired fractions were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-3340e11242c74eebae8cb84808027358
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124780B2

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