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

HRID 413624Notes

Reaction equation

HRID 413624 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2bf4b1d758e74f06b59f832541166b52
Source dataset
uspto-grants-2003_05
Patent number
US06569504B1

Reaction notes

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