4-Bromophenol → HCID 23062453, compound

HRID 2109374

Reaction equation

HRID 2109374 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][C:10]1[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[C:14]([CH3:20])[C:11]=1[CH2:12]Cl.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:20][C:14]1[C:15]([CH3:19])=[CH:16][C:17]([CH3:18])=[C:10]([CH3:9])[C:11]=1[CH2:12][O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 819393-(Chloromethyl)-1,2,4,5-tetramethylbenzene

Product 1

HCID 23062453HCID 23062453, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In acetone (50 ml), a mixture of 4-bromophenol (7.8 g), 2,3,5,6-tetramethylbenzyl chloride (6.3 g) and potassium carbonate (6.5 g) was heated at reflux for 16 hours. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and successively washed with 3% aqueous sodium hydroxide solution, water and saturated brine. The solvent was evaporated under reduced pressure, thereby giving 8.7 g of the desired compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. filtrationThe reaction solution was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washsuccessively washed with 3% aqueous sodium hydroxide solution, water and saturated brine
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-52c09326b92d4d6db679987c70e3e86c
Source dataset
uspto-grants-2009_04
Patent number
US07514452B2

Linked notes

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