4'-Hydroxy-4-biphenylcarboxylic acid → Methyl 4'-hydroxy(1,1'-biphenyl)-4-carboxylate

HRID 1108619Notes

Reaction equation

HRID 1108619 reaction equation
Cl.[CH3:2]O.[OH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1>>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:19]=[CH:18][C:14]([C:15]([O:17][CH3:2])=[O:16])=[CH:13][CH:12]=2)=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 3015564'-Hydroxy-4-biphenylcarboxylic acidHCID 21893726Hydrochloride methanol

Product 1

HCID 1490289Methyl 4'-hydroxy(1,1'-biphenyl)-4-carboxylate

Procedure

15 ml of 10% hydrogen chloride-methanol was added to 1.07 g (5.0 mmol) of 4-(4-hydroxyphenyl)benzoic acid and the mixture was refluxed under heating for 5 hours. After the reaction mixture was concentrated under reduced pressure, water was added thereto and the solution was extracted twice with a chloroform-methanol mixed solution (10:1 (v/v)). The extract was washed with a sodium hydrogencarbonate aqueous solution and dried (MgSO4). The solvent was distilled off to obtain 0.97 g (4.25 mmol) of methyl 4-(4-hydroxyphenyl)benzoate as a faint yellow powder. Its spectroscopic data are as follows:

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 5 hours
  3. concentrationAfter the reaction mixture was concentrated under reduced pressure, water
  4. additionwas added
  5. extractionthe solution was extracted twice with a chloroform-methanol mixed solution (10:1 (v/v))
  6. washThe extract was washed with a sodium hydrogencarbonate aqueous solution
  7. dry with materialdried (MgSO4)
  8. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-fdbc99254a7b43929e2b75ebda350924
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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