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

HRID 655650

Reaktionsgleichung

Reaktionsgleichung von HRID 655650
[BH4-].[Na+].C1COCC1.[Br:8][C:9]1[CH:10]=[C:11]([O:18][CH3:19])[C:12]([OH:17])=[C:13]([CH:16]=1)[CH:14]=[O:15].Cl>C(O)(=O)C>[Br:8][C:9]1[CH:10]=[C:11]([O:18][CH3:19])[C:12]([OH:17])=[C:13]([CH2:14][OH:15])[CH:16]=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 100,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium borohydride (0.28 g, 6.9 mmol) was added to a THF solution (30 ml) of 5-bromo-2-hydroxy-3-methoxybenzaldehyde (3.2 g 13.8 mmol) under ice cooling and the mixture was stirred at 0° C. for 2 hours. Acetic acid was added to the reaction solution to set pH at 3. 10% hydrochloric acid was added to the reaction mixture, which was then extracted with ethyl acetate. The extracted material was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1→1:1) and concentrated to dryness under reduced pressure to obtain 4-bromo-2-hydroxymethyl-6-methoxyphenol (3.23 g) as light yellow oil.

Aufarbeitung

  1. extractionwas then extracted with ethyl acetate
  2. dry with materialThe extracted material was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1→1:1)
  5. concentrationconcentrated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ccc54352225947aa9aa1a81d6c3026d5
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071600B2

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