Potassium Carbonate → 4-(3,4-Dichlorobenzyloxy)-2-methoxybenzaldehyde

HRID 508434Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 508434
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][CH3:11])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=1>CS(C)=O>[Cl:27][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][C:23]=1[Cl:26])[CH2:19][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][CH3:11])[CH:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 5195414-Hydroxy-2-MethoxybenzaldehydeHCID 6397264-(Bromomethyl)-1,2-dichlorobenzene

Produkt 1

HCID 772313794-(3,4-Dichlorobenzyloxy)-2-methoxybenzaldehydeAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A solution of 4-hydroxy-2-methoxybenzaldehyde (300 mg, 1.97 mmol) in DMSO (7.5 mL) was added potassium carbonate (545 mg, 3.94 mmol) the resulting suspension was stirred under nitrogen at room temperature for 10 minutes. 4-(Bromomethyl)-1,2-dichlorobenzene was then added (commercial, 473 mg, 1.32 mmol) and the reaction mixture heated to 90° C. for 3 hours. The reaction mixture was cooled to room temperature and partitioned between EtOAc (50 mL) and water (40 mL). The organic layer was washed with water (2×40 mL), dried over magnesium sulphate and evaporated in vacuo to yield the title compound as a solid (530 mg, 86%):

Aufarbeitung

  1. temperaturethe reaction mixture heated to 90° C. for 3 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. custompartitioned between EtOAc (50 mL) and water (40 mL)
  4. washThe organic layer was washed with water (2×40 mL)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2b817b6f35f349968d0b73e6d79d3ae4
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096500B2

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