Hydrochloric Acid → 3-Chloro-4-hydroxybenzyl alchol

HRID 2041327Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2041327
CC(C[AlH]CC(C)C)C.[Cl:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=1[OH:21])[C:14](OC)=[O:15].Cl>C1(C)C=CC=CC=1>[Cl:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=1[OH:21])[CH2:14][OH:15]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydrideHCID 77580Methyl 3-chloro-4-hydroxybenzoate

Produkt 1

HCID 2574563-Chloro-4-hydroxybenzyl alchol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Add a solution of DIBAL-H in toluene (1.0 M, 35 mL) to a solution of methyl 3-chloro-4-hydroxybenzoate (1.9 g, 10 mmol) at 0° C. under nitrogen. Stir the reaction at 0° C. and gradually warm to ambient temperature overnight. Quench the reaction with slow addition of 0.1N aqueous HCl, add more acid to break the gel-like solid to two clear layers. Separate the organic layer, and extract the aqueous layer with EtOAc three times. Combine the organic layers, wash with brine, dry over Na2SO4, filter and concentrate to give a white solid. MS (ES−) m/z 157 (M−H)−.

Aufarbeitung

  1. customthe reaction at 0° C.
  2. customQuench
  3. customthe reaction
  4. additionadd more acid
  5. customSeparate the organic layer
  6. extractionextract the aqueous layer with EtOAc three times
  7. washCombine the organic layers, wash with brine
  8. dry with materialdry over Na2SO4
  9. filtrationfilter
  10. concentrationconcentrate
  11. customto give a white solid

Quellen und Nachweise

ORD-Eintrag
ord-09ea9bc5c678478796865b7dddb58c5d
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580780B2

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