2',4'-Dihydroxyacetophenone → 1-[4-(3-Chloropropoxy)-2-hydroxyphenyl]-1-ethanone

HRID 263463

Reaction equation

HRID 263463 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].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:8][C:6]1[CH:5]=[CH:4][C:3]([C:9](=[O:11])[CH3:10])=[C:2]([OH:1])[CH:7]=1

Participants

5

Reactant 3

HCID 69902',4'-DihydroxyacetophenoneHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate

Product 1

HCID 17146611-[4-(3-Chloropropoxy)-2-hydroxyphenyl]-1-ethanoneYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

10 g (66 mmole) of 2',4'-dihydroxyacetophenone, 10 ml (101 mmole) of 1-bromo-3-chloropropane and 22.7 g (164 mmole) of anhydrous potassium carbonate in 250 ml of acetone were mixed and refluxed under heating for 16 hours. The mixture was cooled to room temperature, the solid insoluble was separated by filtration, and the filtrate was evaporated to dryness. The residue was dispersed in ethyl ether, filtered and dried to give 13.1 g (87%) of the product, melting point 74° C.

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 16 hours
  3. customthe solid insoluble was separated by filtration
  4. customthe filtrate was evaporated to dryness
  5. additionThe residue was dispersed in ethyl ether
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-6ddbaf6bf6ee49f2989f825a5856d3a5
Source dataset
uspto-grants-1997_07
Patent number
US05643927

Linked notes

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