Methanol → Methyl 4'-hydroxy(1,1'-biphenyl)-4-carboxylate

HRID 369527

Reaktionsgleichung

Reaktionsgleichung von HRID 369527
S(=O)(=O)(O)O.[OH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.O.[CH3:23]O>C1COCC1>[CH3:23][O:20][C:19]([C:16]1[CH:17]=[CH:18][C:13]([C:10]2[CH:9]=[CH:8][C:7]([OH:6])=[CH:12][CH:11]=2)=[CH:14][CH:15]=1)=[O:21]

Komponenten

6

Edukt 4

HCID 887Methanol2×HCID 962WaterHCID 1118Sulfuric AcidHCID 3015564'-Hydroxy-4-biphenylcarboxylic acid

Produkt 1

HCID 1490289Methyl 4'-hydroxy(1,1'-biphenyl)-4-carboxylateAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for three days
  2. customthe solvent was evaporated
  3. filtrationThe resulting solid was filtered
  4. washwashed with water
  5. customrecrystallized
  6. additionwas added to the solution
  7. additionwas added
  8. temperatureAfter cooling
  9. filtrationthe tan precipitate was filtered
  10. washwashed with cold ethanol, and air
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-53bce1ae08354a239459042c108dfb00
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06139771

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