Potassium Carbonate → HCID 13849496, compound

HRID 978124Notes

Reaction equation

HRID 978124 reaction equation
[CH3:1][C:2]([C:4]1[C:5]([OH:11])=[CH:6][CH:7]=[CH:8][C:9]=1[OH:10])=O.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:22])[CH2:20]Br)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([C:20]2[O:10][C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([OH:11])[C:4]=3[C:2]=2[CH3:1])=[O:22])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68303p-Chlorophenacyl bromideHCID 696872',6'-Dihydroxyacetophenone

Product 1

HCID 13849496HCID 13849496, compoundYield 17.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2,6-dihydroxyacetophenone (4.5 g, 30 mmoles), p-chloro-ω-bromoacetophenone (6.9 g, 30 mmoles), potassium carbonate (4.1 g, 30 mmoles) and acetone (100 ml) was refluxed for 7 hours. The mixture was filtered and concentrated. The residue was partitioned between methylene chloride (250 ml) and in sodium hydroxide solution (100 ml). The aqueous phase was separated and acidified with 20% citric acid solution. The precipitated product was filtered and chromatographed to obtain 1.5 g of the title compound, m.p. 238°-241° C.

Workup

  1. temperaturewas refluxed for 7 hours
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. customThe residue was partitioned between methylene chloride (250 ml) and in sodium hydroxide solution (100 ml)
  5. customThe aqueous phase was separated
  6. filtrationThe precipitated product was filtered
  7. customchromatographed

Sources & evidence

ORD record
ord-ed939ab7bc4f4146a3e97e154b60e574
Source dataset
uspto-grants-1987_05
Patent number
US04663347

Reaction notes

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