Triethylamine → 2-Chloromethyl-4,8-dimethoxy-naphthalene

HRID 1858795Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1858795
CS([Cl:5])(=O)=O.[CH3:6][O:7][C:8]1[C:17]2[C:12](=[C:13]([O:18][CH3:19])[CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([CH2:20]O)[CH:9]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:5][CH2:20][C:10]1[CH:9]=[C:8]([O:7][CH3:6])[C:17]2[C:12](=[C:13]([O:18][CH3:19])[CH:14]=[CH:15][CH:16]=2)[CH:11]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22126362HCID 22126362, Verbindung

Produkt 1

HCID 221269642-Chloromethyl-4,8-dimethoxy-naphthaleneAusbeute 88,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 3.92 g of methanesulphonyl chloride in 20 ml of methylene chloride was added dropwise to a solution, cooled to -10° C., of 7.7 g (35.3 mmol) of (4,8-dimethoxy-naphthalen-2-yl)-methanol and 4.4 g (38.8 mmol) of triethylamine in 50 ml of methylene chloride. The reaction mixture was stirred at room temperature for 18 hours. For the working-up, the mixture was extracted with 50 ml of ice-cold sodium hydrogen carbonate solution and the aqueous phase was separated and back-extracted with 25 ml of methylene chloride. The combined organic phases were dried over sodium sulphate and subsequently evaporated under reduced pressure. For purification, the residue was filtered over a layer of silica gel using methylene chloride as the eluent. There were obtained 7.2 g of 2-chloromethyl-4,8-dimethoxy-naphthalene as a beige solid; MS: 296 (M)+.

Aufarbeitung

  1. extractionthe mixture was extracted with 50 ml of ice-cold sodium hydrogen carbonate solution
  2. customthe aqueous phase was separated
  3. extractionback-extracted with 25 ml of methylene chloride
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. customsubsequently evaporated under reduced pressure
  6. customFor purification
  7. filtrationthe residue was filtered over a layer of silica gel

Quellen und Nachweise

ORD-Eintrag
ord-4871e3f6e55f4571828e15067786a104
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06150526

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