Phenol → Benzene, (3-bromopropoxy)-

HRID 1053523Notes

Reaction equation

HRID 1053523 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[Br:14][CH2:15][CH2:16][CH2:17]Br>CC(C)=O>[Br:14][CH2:15][CH2:16][CH2:17][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 80011,3-DibromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 68522Benzene, (3-bromopropoxy)-Yield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Phenol (1.0 g, 10.6 mmol) was dissolved in acetone (20 mL). Anhydrous potassium carbonate (7.34 g, 53.1 mmol) and 1,3-dibromopropane (8.58 g, 42.5 mmol) was added to the solution. The reaction mixture was refluxed in an oil bath for 12 h. After the reaction, the potassium carbonate was removed by suction filtration and solvent was removed under reduced pressure to give the crude product which was then purified by column chromatography using ethyl acetate:hexane (3:7) to give product 26 (2.05 g, 90%). 1H NMR (400 MHz, CDCl3) δ 2.24 (m, 2H), 3.54 (t, J=6.4 Hz, 2H), 4.03 (t, J=5.8 Hz, 2H), 6.86 (m, 3H), 7.21 (m, 2H).

Workup

  1. temperatureThe reaction mixture was refluxed in an oil bath for 12 h
  2. customAfter the reaction
  3. customthe potassium carbonate was removed by suction filtration and solvent
  4. customwas removed under reduced pressure
  5. customto give the crude product which
  6. customwas then purified by column chromatography

Sources & evidence

ORD record
ord-4128366d80d34db5a74e2392f706823f
Source dataset
uspto-grants-2016_07
Patent number
US09393306B2

Reaction notes

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