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

HRID 1193656Notes

Reaction equation

HRID 1193656 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+]>CC(C)=O>[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 chlorideYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 10.6 g (0.637 mole) of 1-(4-hydroxy-2-methoxyphenyl)ethanone, 20 g (0.127 mole) of 1-bromo-3-chloropropane and 26.4 g (0.19 mole) of anhydrous potassium carbonate in 250 ml of acetone was heated at reflux for 20 hr. The mixture was cooled, filtered and the filtrate concentrated under vacuum pump pressure at 90° C. to give an oil which gradually crystallized. The solid was triturated with petroleum ether (30°-60° C.), collected by filtration and dried to yield 14.6 g (94%) of white solid, m.p. 47°-49° C. on recrystallizing from isopropyl ether.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hr
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum pump pressure at 90° C.
  6. customto give an oil which
  7. customgradually crystallized
  8. customThe solid was triturated with petroleum ether (30°-60° C.)
  9. filtrationcollected by filtration
  10. customdried

Sources & evidence

ORD record
ord-ee1e314ef10d4d41bf0cf48d70c7f4e5
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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