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

HRID 1193642Notes

Reaction equation

HRID 1193642 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O-:8])=[O:7])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][CH2:14][Cl:15].[C:16](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:16][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([O:1][CH2:12][CH2:13][CH2:14][Cl:15])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 178524487HCID 178524487, compound

Product 1

HCID 12389265Methyl 4-(3-chloropropoxy)benzoateYield 106.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl, 4-hydroxybenzoate 83.1 g (0.50 mole), 107 ml (1.0 mole) of 1-bromo-3-chloropropane, and potassium carbonate (1.5 mole, 207.3 g) were mechanically stirred in 600 ml of refluxing acetone under nitrogen overnight. The potassium carbonate was removed by filtration, and the filtrate was evaporated under reduced pressure to give 122 g of a liquid. This liquid was dissolved in 250 ml of petroleum ether and with stirring and cooling in an ice/2-propanol bath. A white precipitate formed and was collected by filtration and washed with cold petroleum ether to yield 108 g of a solid. An additional 6 g of the product was obtained from the mother liquor. A small sample of the solid was dissolved in petroleum ether at room temperature. The solution was stirred and cooled in an ice bath. White crystals were collected by filtration, washed with cold petroleum ether and dried under vacuum at room temperature, m.p. 24°-25° C.

Workup

  1. customThe potassium carbonate was removed by filtration
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e679d3abd206479ab2286c7d06ba4102
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

Loading…