Potassium Carbonate → HCID 13912814, compound

HRID 615491Notes

Reaction equation

HRID 615491 reaction equation
[CH3:1][CH2:2][CH2:3][C:4]1[C:9]([OH:10])=[C:8]([C:11]([CH3:13])=[O:12])[CH:7]=[CH:6][C:5]=1[OH:14].Br[CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O.CCOCC>[C:11]([C:8]1[CH:7]=[CH:6][C:5]([O:14][CH2:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=2)=[C:4]([CH2:3][CH2:2][CH3:1])[C:9]=1[OH:10])(=[O:12])[CH3:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Product 1

HCID 13912814HCID 13912814, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 1.0 g (5.15 mmoles) of 2,4-dihydroxy-3-propylacetophenone, see R. A. Appleton et al. in J. Med. Chem. 1977, 20, pages 371-379, and 1.77 g (7.7 mmoles) of methyl 4-bromomethylbenzoate in 20 ml of acetone was treated with 784 mg (5.66 mmoles) of K2CO3 and stirred at reflux for 15 hours. The reaction mixture was diluted with ether, washed with water and saturated aqueous NaHCO3 solution and dried with MgSO4. Evaporation of the solvent gave an oil which crystallized. This material was purified by chromatography on silica gel with 30% hexane/dichloromethane as eluent to provide 1.212 g (69% yield) of the title compound as a white powder mp 99.5°-100.5° C.

Workup

  1. temperatureat reflux for 15 hours
  2. washwashed with water and saturated aqueous NaHCO3 solution
  3. dry with materialdried with MgSO4
  4. customEvaporation of the solvent
  5. customgave an oil which
  6. customcrystallized
  7. customThis material was purified by chromatography on silica gel with 30% hexane/dichloromethane as eluent

Sources & evidence

ORD record
ord-eef6efd322024e6aac4f99792382138b
Source dataset
uspto-grants-1985_02
Patent number
US04499299

Reaction notes

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