4'-Hydroxyacetophenone → HCID 20315614, compound

HRID 2419355Notes

Reaction equation

HRID 2419355 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10].[CH3:15][C:16]([C:18]1[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=1)=[O:17]>CC(C)=O>[C:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:8][C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])=[CH:20][CH:19]=1)(=[O:17])[CH3:15]

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 121593Isopropyl bromoacetate

Product 1

HCID 20315614HCID 20315614, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (17.0g.) was added to a solution of isopropyl bromoacetate (24.0g.) and 4-hydroxyacetophenone (17.7g.) in acetone (200ml.). The mixture was heated under reflux for 24 hours, cooled and filtered. The filtrate was evaporated to an oil which was dissolved in ether (150ml.). The solution was washed with sodium bicarbonate solution (2 × 30ml.), water (2 × 30ml.), dried and evaporated. The residual oil was distilled to give isopropyl 4-acetylphenoxyacetate, I.R. peaks at 1750 and 1670 cm-1.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customThe filtrate was evaporated to an oil which
  6. dissolutionwas dissolved in ether (150ml.)
  7. washThe solution was washed with sodium bicarbonate solution (2 × 30ml.), water (2 × 30ml.)
  8. customdried
  9. customevaporated
  10. distillationThe residual oil was distilled

Sources & evidence

ORD record
ord-4623b85c58ac4ffcb1ff0d3dc1f645c1
Source dataset
uspto-grants-1978_08
Patent number
US04105790

Reaction notes

Loading…