Potassium Carbonate → 4-Chloro-2-(2-methoxy-1-methyl-2-oxoethoxy)benzoic acid, methyl ester

HRID 22197

Reaktionsgleichung

Reaktionsgleichung von HRID 22197
[Cl:1][C:2]1[CH:3]=[C:4]([OH:12])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].Br[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH:15]([CH3:14])[C:16]([O:18][CH3:19])=[O:17])[CH:3]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 76934Methyl 3-bromopropanoateHCID 327085Methyl 4-chloro-2-hydroxybenzoate

Produkt 1

HCID 867465134-Chloro-2-(2-methoxy-1-methyl-2-oxoethoxy)benzoic acid, methyl esterAusbeute 102,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of methyl 4-chlorosalicylate (5.0 g) in dimethyl formamide (10 ml) was treated sequentially with methyl 3-bromopropionate (4.0 g) and potassium carbonate (6.0 g). The mixture was stirred at room temperature for 18 hrs and diluted with water. The mixture was extracted with ether and the organics were washed with water. The organic layer was dried and evaporated to give the desired material (6.7 g) as a low melting solid. NMR: 7.8 (d, 1H), 7.2 (m 1H), 6.9 (m, 1H), 4.8 (q, 1H), 3.9 (s, 3H), 3.8 (s, 3H), 1.7 (d, 3H).

Aufarbeitung

  1. extractionThe mixture was extracted with ether
  2. washthe organics were washed with water
  3. customThe organic layer was dried
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-91b4768fa10d438db6ef5db0120b996e
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428027

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