Phenol → (3-Chloropropoxy)benzene

HRID 722459Notes

Reaction equation

HRID 722459 reaction equation
C([O-])([O-])=O.[K+].[K+].[C:7]1([OH:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[CH2:15][CH2:16][CH2:17][Cl:18]>CC(C)=O>[Cl:18][CH2:17][CH2:16][CH2:15][O:13][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate

Product 1

HCID 76917(3-Chloropropoxy)benzeneYield 96.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 44 g (0.318 mol) of K2CO3 in 300 ml of acetone, 15 g (0.159 mol) of phenol and 18.9 ml (0.191 mol) of 1-bromo-3-chloropropane are added successively at r.t. under N2 atmosphere. The mixture is refluxed for 6 h and concentrated under reduced pressure. The crude mixture is diluted with cold 1 N aqueous NaOH and extracted with AcOEt. The combined extracts are washed with H2O, dried over MgSO4 and concentrated under reduced pressure to give 26.25 g of (3-chloro-propoxy)benzene (yield 83%); NMR (CDCl3): 2.20–2.27 (m, 2H), 3.75 (t, 2H, J=6.04 Hz), 4.11 (t, 2H, J=6.04 Hz), 6.9–6.97 (m, 3H), 7.25–7.31 (m, 2H).

Workup

  1. additionare added successively at r.t. under N2 atmosphere
  2. temperatureThe mixture is refluxed for 6 h
  3. concentrationconcentrated under reduced pressure
  4. additionThe crude mixture is diluted with cold 1 N aqueous NaOH
  5. extractionextracted with AcOEt
  6. washThe combined extracts are washed with H2O
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8ec6f0a4018d4934a828754098fc8c20
Source dataset
uspto-grants-2006_11
Patent number
US07138432B1

Reaction notes

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