Thionyl Chloride → Methyl 2-(4'-chloromethylphenyl)benzoate

HRID 744973Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 744973
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1.S(Cl)([Cl:21])=O>N1C=CC=CC=1.C(Cl)Cl>[Cl:21][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1

Komponenten

5

Edukt 2

HCID 24386Thionyl ChlorideHCID 15380881Methyl 4'-(hydroxymethyl)-[1,1'-biphenyl]-2-carboxylate

Produkt 1

HCID 15380884Methyl 2-(4'-chloromethylphenyl)benzoateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2.0 g (8.25 mmol) of methyl 2-(4'-hydroxymethylphenyl)benzoate was dissolved in 1.31 g of pyridine and methylene chloride (20 ml). 1.47 g (12.4 mmol) of thionyl chloride was dropwise added thereto at room temperature, followed by stirring as such for 16 hours and under reflux by heating for 5 hours. After the reaction liquid was cooled and concentrated, a saturated aqueous solution of sodium hydrogencarbonate was added thereto, followed by the extraction with methylene chloride. The organic phase was washed with water, dried and subjected to vacuum concentration. The residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system) to give 1.89 g of the title compound as an oil (yield 88%).

Aufarbeitung

  1. customat room temperature
  2. temperatureunder reflux
  3. temperatureby heating for 5 hours
  4. customAfter the reaction liquid
  5. temperaturewas cooled
  6. concentrationconcentrated
  7. additiona saturated aqueous solution of sodium hydrogencarbonate was added
  8. extractionfollowed by the extraction with methylene chloride
  9. washThe organic phase was washed with water
  10. customdried
  11. concentrationsubjected to vacuum concentration
  12. customThe residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system)

Quellen und Nachweise

ORD-Eintrag
ord-837cb63b62f24b8aa6771c2b3d3d74b2
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05559236

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