Reaktion #77525

Reaktionsgleichung

2-allyloxy-4-(benzyloxy)benzaldehyde

m-chloroperoxybenzoic acid

→

title compound

Ausbeute 64.4%

2-Allyloxy-4-(benzyloxy)phenol

Ausbeute 64.4%

Lösungsmittel

methylene chloride

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed four times with 500 mL portions of saturated aqueous sodium bicarbonate
2. 2
   Trocknendried over magnesium sulfate
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated in vacuum to a brown oil
5. 5
   workup.DISSOLUTIONThis was redissolved in 1 L of methanol
6. 6
   workup.ADDITION110 g of basic alumina added
7. 7
   workup.STIRRINGthe mixture stirred at room temperature for 15 hours
8. 8
   SonstigeThe alumina was removed by filtration
9. 9
   Einengenthe filtrate concentrated to 50 g of a yellow solid
10. 10
    Sonstigechromatographed on silica gel with hexane/methylene chloride as eluant

Vorschrift

To a solution of 53.6 g (0.20 mole) of 2-allyloxy-4-(benzyloxy)benzaldehyde in 500 mL of methylene chloride was added a solution of 90 g (˜0.3 mole) of 57-86% m-chloroperoxybenzoic acid in 500 mL of methylene chloride. The mixture was stirred at room temperature for 3 days. It was then diluted to 2 L with methylene chloride and washed four times with 500 mL portions of saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated in vacuum to a brown oil. This was redissolved in 1 L of methanol, 110 g of basic alumina added and the mixture stirred at room temperature for 15 hours. The alumina was removed by filtration and the filtrate concentrated to 50 g of a yellow solid. The crude solid was column chromatographed on silica gel with hexane/methylene chloride as eluant to give 33 g of the title compound as a white solid, m.p. 62° C.

Quelle