Benzyl Chloride → 3-Benzyloxy-4-hydroxybenzaldehyde

HRID 1356216

Reaktionsgleichung

Reaktionsgleichung von HRID 1356216
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[H-].[Na+].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[CH2:13]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

5

Edukt 3

HCID 7503Benzyl ChlorideHCID 87683,4-DihydroxybenzaldehydeHCID 24758Sodium hydride

Produkt 1

HCID 110206353-Benzyloxy-4-hydroxybenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

3,4-Dihydroxybenzaldehyde (30.2 g, 219 mmol) is dissolved in DMF (300 mL) and added to a suspension of NaH (60% oil, 17.2 g, 430 mmol) in DMF (500 mL) at RT. The mixture is stirred for 30 minutes and benzyl chloride (17.3 mL, 150 mmol) is added at 0° C. The reaction is stirred overnight. The solvent is removed by evaporation and the residue is dissolved in water (500 mL). The mixture is extracted three times with CH2Cl2. The aqueous layer is acidified with HOAC (100 mL). The product is precipitated and filtered, washed with water to provide 3-benzyloxy-4-hydroxybenzaldehyde.

Aufarbeitung

  1. stirringThe reaction is stirred overnight
  2. customThe solvent is removed by evaporation
  3. dissolutionthe residue is dissolved in water (500 mL)
  4. extractionThe mixture is extracted three times with CH2Cl2
  5. customThe product is precipitated
  6. filtrationfiltered
  7. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-0fc36350b4254cfa8b2324171dd7f381
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586467B2

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