Acetic Acid → 2,6-Dimethylbiphenyl-4-ol

HRID 414614Notes

Reaction equation

HRID 414614 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[C:4]([CH3:10])[C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(O)(=O)C.Br>O>[CH3:10][C:4]1[CH:5]=[C:6]([OH:8])[CH:7]=[C:2]([CH3:1])[C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 135430144-Methoxy-2,6-dimethyl-1,1'-biphenyl

Product 1

HCID 218306382,6-Dimethylbiphenyl-4-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,6-dimethyl-4-methoxybiphenyl (3.0 g), acetic acid (30 ml) and 48% aqueous hydrobromic acid (30 ml) were heated at reflux temperature for 4 hours. The mixture was then cooled, poured into water and extracted with ether. After extracting the organic solution with aqueous sodium hydroxide, the aqueous extract was acidified with aqueous hydrochloric acid and further extracted with ether. The resulting extract was dried and evaporated and the residue was recrystallized from acetone/hexane to afford 2,6-dimethyl-4-hydroxybiphenyl, mp 128°-130° C.

Workup

  1. temperatureat reflux temperature for 4 hours
  2. temperatureThe mixture was then cooled
  3. extractionextracted with ether
  4. extractionAfter extracting the organic solution with aqueous sodium hydroxide
  5. extractionthe aqueous extract
  6. extractionfurther extracted with ether
  7. extractionThe resulting extract
  8. customwas dried
  9. customevaporated
  10. customthe residue was recrystallized from acetone/hexane

Sources & evidence

ORD record
ord-81bbee06159849029618a7089b6cf1de
Source dataset
uspto-grants-1988_12
Patent number
US04792570

Reaction notes

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