Chloromethyl Methyl Ether → Ethyl 3-bromo-4-methoxymethoxybenzoate

HRID 13259

Reaktionsgleichung

Reaktionsgleichung von HRID 13259
[H-].[Na+].[O:3]1[CH2:7]CC[CH2:4]1.[Br:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=1[OH:20])[C:12]([O:14][CH2:15][CH3:16])=[O:13].COCCl>C(OCC)(=O)C>[Br:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=1[O:20][CH2:4][O:3][CH3:7])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Komponenten

6

Edukt 4

HCID 7864Chloromethyl Methyl EtherHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 4778964Ethyl 3-bromo-4-hydroxybenzoate

Produkt 1

HCID 23145548Ethyl 3-bromo-4-methoxymethoxybenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5.5 g of sodium hydride was added to a tetrahydrofuran (300 ml) solution of 20.5 g of ethyl 3-bromo-4-hydroxybenzoate produced according to the method described in Monatsh. Chem.; 22; 1901; 437, with cooling with ice, and the reaction liquid was stirred for 30 minutes, and then, at the same temperature, 10 ml of chloromethyl methyl ether was added to the reaction liquid, and the reaction liquid was stirred overnight at room temperature. The reaction liquid was diluted with ethyl acetate, and washed with water, and the aqueous layer was extracted with ethyl acetate, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting solid was suspended in hexane and then taken out through filtration to obtain the entitled compound as a white solid.

Aufarbeitung

  1. customproduced
  2. temperature437, with cooling with ice
  3. customthe reaction liquid
  4. customthe reaction liquid
  5. stirringwas stirred overnight at room temperature
  6. customThe reaction liquid
  7. washwashed with water
  8. extractionthe aqueous layer was extracted with ethyl acetate
  9. dry with materialdried with anhydrous magnesium sulfate
  10. customThe solvent was evaporated away under reduced pressure
  11. filtrationtaken out through filtration

Quellen und Nachweise

ORD-Eintrag
ord-39773446c1b64b71b3c66c90f66f485a
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728025B2

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