Dimethyl Sulfate → 4-Benzyloxy-2-methoxy-3-methyl-benzaldehyde

HRID 561917Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 561917
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([OH:17])[C:10]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19]OS(OC)(=O)=O.[OH-].[Na+].O1CCOCC1>O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([O:17][CH3:19])[C:10]=1[CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 597616904-(Benzyloxy)-2-hydroxy-3-methylbenzaldehyde

Produkt 1

HCID 597617644-Benzyloxy-2-methoxy-3-methyl-benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 4-benzyloxy-2-hydroxy-3-methyl-benzaldehyde (1.57 g, 6.49 mmol), dimethylsulfate (1.04 ml, 10.9 mmol), NaOH (1.02 g, 25.5 mmol), 1,4-dioxane (20 mL) and water (10 mL) was stirred at 90° C. for 6 h. The reaction mixture was cooled to RT, water (100 mL) was added, extracted with EtOAc (150 mL). The extract was washed with brine (100 mL), dried over Na2SO4 and evaporated. The residue was purified on SiO2 (25 g) column, hexane to toluene. Yield 1.20 g (4.68 mmol, 72%), white solid. 1H NMR (300 MHz, DMSO): δ 10.11 (s, 1H), 7.64 (d, J=8.9 Hz, 1H), 7.49-7.32 (m, 5H), 7.05 (d, J=8.9 Hz, 1H), 5.24 (s, 2H), 3.81 (s, 3H), 2.14 (s, 3H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionextracted with EtOAc (150 mL)
  3. washThe extract was washed with brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified on SiO2 (25 g) column, hexane to toluene

Quellen und Nachweise

ORD-Eintrag
ord-3311f4c851624553b0bc50ddb39b22ec
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063225B2

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