1-Bromo-3-chloropropane → 1-[4-(3-Chloropropoxy)-3-methylphenyl]ethanone

HRID 1193649Notes

Reaction equation

HRID 1193649 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].Br[CH2:13][CH2:14][CH2:15][Cl:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:16][CH2:15][CH2:14][CH2:13][O:11][C:3]1[CH:4]=[CH:5][C:6]([C:8](=[O:9])[CH3:10])=[CH:7][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 701354'-Hydroxy-3'-methylacetophenone

Product 1

HCID 144071751-[4-(3-Chloropropoxy)-3-methylphenyl]ethanoneYield 95.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 25 g (0.166 mole) of 4-hydroxy-3-methylacetophenone, 45.8 g (0.33 mole) of 1-bromo-3-chloropropane and 69.1 g (0.5 mole) of anhydrous potassium carbonate in 500 ml of acetone was heated at reflux for 20 hr. The mixture was cooled, filtered, and the filtrate concentrated under reduced pressure to give an oil as residue. The oil was crystallized in petroluem ether. The solid was collected by filtration, washed with petroleum ether and dried to yield 35.8 g (95%) of an off-white powder. An analytical sample, m.p. 41.5°-42.5° C. was prepared from petroleum ether.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hr
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customto give an oil as residue
  7. customThe oil was crystallized in petroluem ether
  8. filtrationThe solid was collected by filtration
  9. washwashed with petroleum ether
  10. customdried

Sources & evidence

ORD record
ord-829dc3e901ef4d2dac2b82cc6015a0ee
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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