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

HRID 2072631Notes

Reaction equation

HRID 2072631 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-b1bd56b99866417bbb9a79a4510633a1
Source dataset
uspto-grants-1990_04
Patent number
US04913839

Reaction notes

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