Water → Benzene, ((6-bromohexyl)oxy)-

HRID 344243Notes

Reaction equation

HRID 344243 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br.O>CN(C)C=O>[O:9]([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][Br:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 123681,6-DibromohexaneHCID 24758Sodium hydride

Product 1

HCID 142878Benzene, ((6-bromohexyl)oxy)-Yield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

60% Sodium hydride (1.16 g) was suspended in dimethylformamide (40 ml), and phenol (3 g) was added under ice-cooilng with stirring. The mixture was stirred at room temperature for 1 hr. The mixture was again ice-cooled, and a solution of 1,6-dibromohexane (7.78 g) in dimethylformamide (10 ml) was dropwise added, which was followed by stirring at room temperature for 2 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and the solvent was evaporated under reduced pressure to give 8.2 g of 6-phenoxyhexyl bromide.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hr
  2. temperaturecooled
  3. stirringby stirring at room temperature for 2 hr
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. customdried
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3dd84a54b3354a97be045c421743f8ac
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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