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

HRID 1709833Notes

Reaction equation

HRID 1709833 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-3ece2d255281492192ed5b5d16cbe6f4
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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