Bromomethyl 4-methoxyphenyl ketone → HCID 15373528, compound

HRID 1414617Notes

Reaction equation

HRID 1414617 reaction equation
[CH:1](=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[OH-].[K+].Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)=[O:15]>CO>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]([C:13]2[O:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[CH:1]=2)=[O:15])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 6998SalicylaldehydeHCID 14797Potassium Hydroxide

Product 1

HCID 15373528HCID 15373528, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To 11.0 g. (0.09 mol.) of salicylaldehyde in 30 ml. of dry methanol was added 5.1 g. (0.09 mol.) of potassium hydroxide dissolved in 50 ml. of methanol. The solution was refluxed for 10 minutes and 20.5 g. (0.09 mol.) of α-bromo-p-methoxyacetophenone dissolved in 50 ml. of warm methanol was added dropwise but rapidly over a 10 minute interval. The resulting solution was refluxed for one hour, then filtered and concentrated. The residue was dissolved in ether and the ether solution was washed with water. The aqueous washings were extracted twice with ether and the ethereal extracts were combined, reduced in volume, refluxed with decolorizing carbon, filtered, dried (MgSO4) and concentrated to give 2-(4'-methoxybenzoyl)benzofuran which was recrystallized from isopropanol, m.p. 93°-94°.

Workup

  1. temperatureThe solution was refluxed for 10 minutes
  2. temperatureThe resulting solution was refluxed for one hour
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in ether
  6. washthe ether solution was washed with water
  7. extractionThe aqueous washings were extracted twice with ether
  8. temperaturerefluxed with decolorizing carbon
  9. filtrationfiltered
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-0dbca3790f104367b68a5ad1f12fd07a
Source dataset
uspto-grants-1977_01
Patent number
US04001426

Reaction notes

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