Hydrochloric Acid → 2-Hydroxy-4-methoxy-3-methylbenzaldehyde

HRID 854867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 854867
C[O:2][C:3]1[C:10]([CH3:11])=[C:9]([O:12][CH3:13])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].[Cl-].[Be+2].[Cl-].Cl>C1(C)C=CC=CC=1>[OH:2][C:3]1[C:10]([CH3:11])=[C:9]([O:12][CH3:13])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 24588Beryllium ChlorideHCID 2516932,4-Dimethoxy-3-methylbenzaldehyde

Produkt 1

HCID 105112462-Hydroxy-4-methoxy-3-methylbenzaldehydeAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 2,4-dimethoxy 3-methyl benzaldehyde (3.75 g, 20.8 mmole) and beryllium chloride (5.0 g, 62.5 mmole) in anhydrous toluene (50 mL) was heated to reflux for 3.5 hour. The solvent was evaporated under reduced pressure to yield an orange residue, which was treated with 2 N HCl. The compound was extracted with methylene chloride and the organic layer was dried over anhydrous MgSO4. The filtrate was evaporated and dried in vacuo to give an orange solid (3.4 g, 99%): LCMS m/z 168.05 (M+H). 1H NMR (CDCl3/300 MHz) 11.45 (s, 1H), 9.72 (s, 1H), 7.37 (d, 1H, J=8.7 Hz), 6.57 (d, 1H, J=8.7 Hz), 3.92 (s, 3H), 2.10 (s, 3H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 3.5 hour
  3. customThe solvent was evaporated under reduced pressure
  4. customto yield an orange residue, which
  5. extractionThe compound was extracted with methylene chloride
  6. dry with materialthe organic layer was dried over anhydrous MgSO4
  7. customThe filtrate was evaporated
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6dd9123059864af29f6a404503578d21
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259266B2

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