Phenol → (3-Chloropropoxy)benzene

HRID 1662987Notes

Reaction equation

HRID 1662987 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 1N 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 1N 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-f109d92a6d1649e7bfea588a29fdeab1
Source dataset
uspto-grants-2011_10
Patent number
US08034810B2

Reaction notes

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