Benzyl Bromide → 4-(Benzyloxy)-2-hydroxy-3-methylbenzaldehyde

HRID 561916

Reaktionsgleichung

Reaktionsgleichung von HRID 561916
[OH:1][C:2]1[C:9]([CH3:10])=[C:8]([OH:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+].O1CCOCC1>O>[CH2:12]([O:11][C:8]1[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([OH:1])[C:9]=1[CH3:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 7498Benzyl BromideHCID 312751,4-DioxaneHCID 803952,4-Dihydroxy-3-methylbenzaldehydeHCID 516892Sodium Bicarbonate

Produkt 1

HCID 597616904-(Benzyloxy)-2-hydroxy-3-methylbenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 2,4-dihydroxy-3-methyl-benzaldehyde (3.31 g, 21.8 mmol), benzylbromide (4.09 g, 23.9 mmol), NaHCO3 (5.49 g, 65.4 mmol), 1,4-dioxane (30 mL) and water (12 mL) was stirred at 60° C. for overnight. Then the reaction mixture was cooled to RT, water (100 mL) was added, extracted with EtOAc (2×200 mL). The extract was dried over Na2SO4, evaporated. The residue was purified on SiO2 (25 g) column, hexane-EtOAc (0 to 5%). Yield 1.57 g (6.48 mmol, 29%) as off-white solid.

Aufarbeitung

  1. temperatureThen the reaction mixture was cooled to RT
  2. extractionextracted with EtOAc (2×200 mL)
  3. dry with materialThe extract was dried over Na2SO4
  4. customevaporated
  5. customThe residue was purified on SiO2 (25 g) column, hexane-EtOAc (0 to 5%)

Quellen und Nachweise

ORD-Eintrag
ord-4e2869e8413849ad91e67fd6dc8aed26
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063225B2

Verknüpfte Notizen

Wird geladen…