Hydrogen Bromide → 4'-Hydroxy-4-biphenylcarboxylic acid

HRID 442577Notes

Reaction equation

HRID 442577 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.Br>C(O)(=O)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 27595524'-Methoxy(1,1'-biphenyl)-4-carboxylic acid

Product 1

HCID 3015564'-Hydroxy-4-biphenylcarboxylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred mixture of compound 2 (27.00 g, 0.118 mol) and hydrobromic acid (48% w/v, 350 ml) in glacial acetic acid (600 ml) was heated under reflux for 6 h. The cooled solution was poured into an ice/water mixture (1 l) and the resulting white precipitate was filtered off and washed with water until acid-free. Recrystallisation from glacial acetic acid afforded white crystals which were dried over potassium hydroxide in vacuo.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 h
  3. filtrationthe resulting white precipitate was filtered off
  4. washwashed with water until acid-free
  5. customRecrystallisation from glacial acetic acid afforded white crystals which
  6. dry with materialwere dried over potassium hydroxide in vacuo

Sources & evidence

ORD record
ord-c198072a0ad245a78635c20516faa838
Source dataset
uspto-grants-1999_04
Patent number
US05891358

Reaction notes

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