Benzyl Chloride → 2-(Benzyloxy)-N,N-dimethylbenzamide

HRID 1037660

Reaktionsgleichung

Reaktionsgleichung von HRID 1037660
[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH2:19]([O:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 745002-Hydroxy-N,N-dimethylbenzamide

Produkt 1

HCID 130736022-(Benzyloxy)-N,N-dimethylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In an argon atmosphere, a mixture of 6.55 g (39.7 mmol) of 15, 10.9 g (79.3 mmol) of K2CO3, 1.0 g (5.94 mmol) of KI and 80 mL of anhydrous DMF was stirred for 10 min at room temperature. After that 7.52 g (59.5 mmol) of benzyl chloride was added in one portion. The resulting mixture was stirred for 2 hr at 70° C. and then evaporated to dryness. To the residue, 70 mL of water and 30 mL of dichloromethane were added. The organic layer was separated, and the aqueous layer was washed by 2×50 mL of dichloromethane. The combined organic extract was dried over Na2SO4 and then evaporated to dryness. The residue was washed by 50 mL of cold ether and dried in vacuum. Yield 9.71 g (96%) of a white solid.

Aufarbeitung

  1. stirringThe resulting mixture was stirred for 2 hr at 70° C.
  2. customevaporated to dryness
  3. additionTo the residue, 70 mL of water and 30 mL of dichloromethane were added
  4. customThe organic layer was separated
  5. washthe aqueous layer was washed by 2×50 mL of dichloromethane
  6. extractionThe combined organic extract
  7. dry with materialwas dried over Na2SO4
  8. customevaporated to dryness
  9. washThe residue was washed by 50 mL of cold ether
  10. customdried in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-21dbb1cece184c71aed5c3aeab22a8fa
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546501B2

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