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

HRID 268703Notes

Reaction equation

HRID 268703 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+]>CC(C)=O>[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)benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl 4-hydroxybenzoate (60.0 g), 1-bromo-3-chloropropane (71.37 ml) and potassium carbonate (149.61 g) were heated under reflux in acetone (1445 ml) overnight. The reaction mixture was then allowed to cool to rt, filtered and evaporated. The residue was chromatographed [silica gel; step gradient 0-5% ethyl acetate/hexane]. Fractions containing pure product were combined and evaporated to give the subtitled compound as a clear oil (70.0 g). MS electrospray (+ion) 243 (MH+). 1H NMR δ (CDCl3): 8.00 (2H, d, J=8.8 Hz), 6.92 (2H, d, J=8.8 Hz), 4.36 (2H, q, J=7.1 Hz), 4.18 (2H, t, J=5.8 Hz), 3.74 (2H, t, J=6.2), 2.25 (2H, m), 1.37 (3H, t, J=7.1 Hz).

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customThe residue was chromatographed [silica gel; step gradient 0-5% ethyl acetate/hexane]
  4. additionFractions containing pure product
  5. customevaporated

Sources & evidence

ORD record
ord-4b1266b4c0a54aa183d5e20eefbdd13a
Source dataset
uspto-grants-2008_11
Patent number
US07446103B2

Reaction notes

Loading…