4,4'-Dihydroxybiphenyl → 4'-(2-Methylbutoxy)(1,1'-biphenyl)-4-ol

HRID 231005

Reaction equation

HRID 231005 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:15][CH:16]([CH2:19][CH3:20])[CH2:17]Br.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:15][CH:16]([CH2:19][CH3:20])[CH2:17][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 71124,4'-DihydroxybiphenylHCID 11430Potassium CarbonateHCID 252541-Bromo-2-methylbutane

Product 1

HCID 140938154'-(2-Methylbutoxy)(1,1'-biphenyl)-4-olYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.20 mole(37.2 g) of 4,4'-dihydroxybiphenyl, 0.10 mole(15.1 g) of the above 2-methyl-1-bromobutane, and 0.60 mole(33.7 g) of potassium carbonate in 300 ml of ethanol was refluxed for 16 hours. After the reaction, the reaction solution was filtered and concentrated, then purified by column chromatography to obtain 4.9 g of 4'-(2-methylbutoxy)-4-hydroxybiphenyl. (yield: 58%)

Workup

  1. customAfter the reaction
  2. filtrationthe reaction solution was filtered
  3. concentrationconcentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-7579d4eec5224c2fa2bdb88004109b17
Source dataset
uspto-grants-1989_07
Patent number
US04844835

Linked notes

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