HCID 21424222, compound → 4-(1-Methylethyl)(1,1'-biphenyl)-2-ol

HRID 259302Notes

Reaction equation

HRID 259302 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([O:16]C)[CH:5]=1)([CH3:3])[CH3:2]>Br.C(O)(=O)C.O>[OH:16][C:6]1[CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:9]=[CH:8][C:7]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 1

HCID 21424222HCID 21424222, compound

Product 1

HCID 64531574-(1-Methylethyl)(1,1'-biphenyl)-2-ol

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

A mixture of 4-isopropyl-2-methoxybiphenyl (3.8g from Example 5) in aqueous hydrobromic acid (150ml; 48%) and acetic acid (glacial, 50ml) was stirred under reflux for 7 hours. The mixture was cooled, diluted with water and extracted with ether. The extract was washed with water, dried, evaporated and distilled to give 2-hydroxy-4-isopropylbiphenyl, b.p. 112°-113°/0.2 mm.

Workup

  1. temperatureunder reflux for 7 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted with ether
  4. washThe extract was washed with water
  5. customdried
  6. customevaporated
  7. distillationdistilled

Sources & evidence

ORD record
ord-fdd54c9d293d44218bce3bc4d04a9bf2
Source dataset
uspto-grants-1977_07
Patent number
US04036989

Reaction notes

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