Hydrochloric Acid → 4-Bromo-2-(hydroxymethyl)-6-methoxyphenol

HRID 1161402Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1161402
[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].C1COCC1.[BH4-].[Na+].Cl>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([OH:10])=[C:6]([CH2:7][OH:8])[CH:9]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 2622385-Bromo-2-hydroxy-3-methoxybenzaldehydeHCID 4311764Sodium borohydride

Produkt 1

HCID 8940924-Bromo-2-(hydroxymethyl)-6-methoxyphenolAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 50 g of 5-bromo-2-hydroxy-3-methoxybenzaldehyde in 200 ml of an ethanol:THF=1:1 mixed solvent there was added 16.4 g of sodium borohydride while cooling on ice. After stirring at room temperature for 2 hours, 1N hydrochloric acid was added to the reaction mixture while cooling on ice. The organic layer was washed with ethyl acetate and dried over anhydrous magnesium sulfate. The desiccating agent was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (50 g) as a crude product.

Aufarbeitung

  1. temperaturewhile cooling on ice
  2. temperaturewhile cooling on ice
  3. washThe organic layer was washed with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe desiccating agent was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f70b09cfff0e422789fe0e0e9bd0e158
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816522B2

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