1-Bromo-3-chloropropane → 3-(p-Acetyl-m-methoxyphenoxy)propyl chloride

HRID 2042633Notes

Reaction equation

HRID 2042633 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([O:11][CH3:12])[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:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 529402Isopeonol

Product 1

HCID 144071823-(p-Acetyl-m-methoxyphenoxy)propyl chloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a 250 mL round bottom flask, 1-(4-hydroxy-2-methoxy-phenyl)ethanone (5.0 g, 30.0 mmol), 1-bromo-3-chloro-propane (3.27 mL, 33.1 mmol), and potassium carbonate (4.75 g, 33.1 mmol) in acetonitrile (100 mL) was heated to reflux 14 h. The reaction was cooled and the solvent concentrated under vacuum. The slurry was partitioned between methylene chloride and water, separated, dried over MgSO4. Purification with silica gel chromatography eluting with hexanes/ethyl acetate (3:1) produced 6.18 g (85%). Mp 51-53° C. MS m/z 243 (M+H).

Workup

  1. temperatureto reflux 14 h
  2. temperatureThe reaction was cooled
  3. concentrationthe solvent concentrated under vacuum
  4. customThe slurry was partitioned between methylene chloride and water
  5. customseparated
  6. dry with materialdried over MgSO4
  7. customPurification with silica gel chromatography
  8. washeluting with hexanes/ethyl acetate (3:1)
  9. customproduced 6.18 g (85%)

Sources & evidence

ORD record
ord-7fd30d4a09da41a6ae4fdfca4b748c80
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

Loading…