Phenol → HCID 18347201, compound

HRID 2269565Notes

Reaction equation

HRID 2269565 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)=[O:11].C([O-])([O-])=O.[K+].[K+]>CC(C)=O.CCCCCC.CCOC(C)=O>[O:7]([CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)=[O:11])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 27375232-Bromo-1-(4-methylsulfanylphenyl)ethanone

Product 1

HCID 18347201HCID 18347201, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of phenol (9.4 g) and 2-bromo-1-(4-(methylthio)phenyl)ethanone (12.5 g) in 500 mL of acetone was added K2CO3 (13.8 g). The mixture was refluxed for 12 h, then diluted with 500 mL of 1:1 hexane/EtOAc. The solid was removed by filtration and the filtrate was concentrated. The residue was dissolved in Et2O (500 mL), washed with 1N NaOH (100 ml) and dried over MgSO4. After filtration and concentration, the title compound (9 g) was collected by filtration and air dried.

Workup

  1. temperatureThe mixture was refluxed for 12 h
  2. customThe solid was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in Et2O (500 mL)
  5. washwashed with 1N NaOH (100 ml)
  6. dry with materialdried over MgSO4
  7. filtrationAfter filtration and concentration
  8. filtrationthe title compound (9 g) was collected by filtration and air
  9. customdried

Sources & evidence

ORD record
ord-751651874417468293329595a7611527
Source dataset
uspto-grants-2001_12
Patent number
US06329421B1

Reaction notes

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