Reaktion #456709

Reaktionsgleichung

sulfuric acid

4'-hydroxy-4-biphenylcarboxylic acid

methanol

methanol

water

→

tan solid

Ausbeute 86.0%

Methyl-4'-hydroxy-4-biphenylcarboxylate

Ausbeute 86.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was refluxed for three days
2. 2
   Sonstigethe solvent was evaporated
3. 3
   FiltrationThe resulting solid was filtered
4. 4
   Waschenwashed with water
5. 5
   Sonstigerecrystallized
6. 6
   workup.ADDITIONwas added to the solution
7. 7
   workup.ADDITIONwas added
8. 8
   TemperaturAfter cooling
9. 9
   Filtrationthe tan precipitate was filtered
10. 10
    Waschenwashed with cold ethanol, and air
11. 11
    Sonstigedried

Vorschrift

Concentrated sulfuric acid (approximately 4 ml) was carefully added to a solution of 4'-hydroxy-4-biphenylcarboxylic acid (Aldrich) (8.20 g, 38.3 mmol) in 1 liter of methanol. The reaction mixture was refluxed for three days and the solvent was evaporated. The resulting solid was filtered, washed with water, and recrystallized as follows. The crude solid was dissolved in a minimum amount of hot THF, and approximately three equivalents of methanol was added to the solution. The solution was brought to a boil, and water was added with vigorous stirring until the solution remained cloudy. After cooling, the tan precipitate was filtered, washed with cold ethanol, and air dried to yield 7.57 g (86%) of a tan solid.

Quelle