1-Bromo-3-chloropropane → Ethyl 4-(3-chloropropoxy)benzoate

HRID 2268481Notes

Reaction equation

HRID 2268481 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.Br[CH2:14][CH2:15][CH2:16][Cl:17].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:17][CH2:16][CH2:15][CH2:14][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 8434EthylparabenHCID 11430Potassium Carbonate

Product 1

HCID 18348522Ethyl 4-(3-chloropropoxy)benzoateYield 91.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

The mixture of ethyl 4-hydroxybenzoate(50.0 g), 1-bromo-3-chloropropane (56.8 g), and potassium carbonate (125 g) in acetonitrile (500 ml) was stirred 40° C. for 48 hr. The reaction mixture was concentrated and the residue was diluted with water, then extracted with diethyl ether. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was purified by alumina column chromatography (hexane to hexane:ethyl acetate=20:1) to yield the entitled compound (66.5 g) as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with water
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with water and saturated aqueous sodium chloride
  5. customdried
  6. customThe solvent was removed in vacuo
  7. customThe residue was purified by alumina column chromatography (hexane to hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-5db7ea18ebdd41678f841d7b91d6cf2b
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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