Acetic Acid → 4,4′-Dihydroxy[1,1′-biphenyl]-3-carboxylic acid

HRID 1838785Notes

Reaction equation

HRID 1838785 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14]C)=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:16]([OH:18])=[O:17].C(O)(=O)C.Br>[Br-].C([P+](CCCC)(CCCC)CCCC)CCC.O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=2)=[CH:4][C:3]=1[C:16]([OH:18])=[O:17]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 51971334-Hydroxy-4′-methoxy[1,1′-biphenyl]-3-carboxylic acid

Product 1

HCID 234484124,4′-Dihydroxy[1,1′-biphenyl]-3-carboxylic acidYield 48.3%

Reagents, catalysts & solvents 2

HCID 76564Tetrabutylphosphonium bromideCatalystHCID 962WaterSolvent

Procedure

A solution of 4-hydroxy-4′-methoxy-3-biphenylcarboxylic acid (5.3 g; 21.6 mmol), tetrabutylphosphonium bromide (0.8 g; 2.3 mmol), acetic acid (35 ml) and hydrobromic acid (35 ml of a 48% solution) was heated at reflux for 6 h. The reaction mixture was cooled and poured into water (400 ml). The resulting precipitate was isolated and recrystallised from ethyl acetate to give 2.4 g (47%) of 4,4′-dihydroxy-3-biphenyl-carboxylic acid.

Workup

  1. temperatureat reflux for 6 h
  2. temperatureThe reaction mixture was cooled
  3. customThe resulting precipitate was isolated
  4. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-a8468112a53940b59cdcc25b28d54e59
Source dataset
uspto-grants-2004_01
Patent number
US06676851B1

Reaction notes

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