Potassium Carbonate → 2-(p-Methoxybenzoyl)-3-methyl-4-hydroxybenzofuran

HRID 1534238Notes

Reaction equation

HRID 1534238 reaction equation
[CH3:1][C:2]([C:4]1C(O)=[CH:6][CH:7]=[CH:8][C:9]=1[OH:10])=O.[C:12](=O)([O-])[O-:13].[K+].[K+].[CH3:18][O:19][CH:20](Br)[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:22]>CC(C)=O>[CH3:12][O:13][C:26]1[CH:27]=[CH:28][C:23]([C:21]([C:20]2[O:19][C:18]3[CH:1]=[CH:2][CH:4]=[C:9]([OH:10])[C:8]=3[C:7]=2[CH3:6])=[O:22])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 696872',6'-DihydroxyacetophenoneHCID 15556716Methoxyphenacylbromide

Product 1

HCID 145797912-(p-Methoxybenzoyl)-3-methyl-4-hydroxybenzofuranYield 65.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2,6-dihydroxyacetophenone (5.35 gm; 35.0 mmoles), potassium carbonate (4.83 gm; 35.0 mmoles), and p methoxyphenacylbromide (8.05 gm; 35.0 mmoles) in acetone (150 mL) was refluxed for a period of 22 hours. The reaction mixture was cooled, filtered through Celite, and concentrated in vacuo. The residue was dissolved in methylene chloride and washed with IN sodium hydroxide. The aqueous phase was then acidified with 20% citric acid. The solid was filtered, washed with water, and air dried to yield 6.5 gm (65%) of 2-(p-methoxybenzoyl)-3-methyl-4-hydroxybenzofuran, mp. 192°-195° C.

Workup

  1. temperaturewas refluxed for a period of 22 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through Celite
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in methylene chloride
  6. washwashed with IN sodium hydroxide
  7. filtrationThe solid was filtered
  8. washwashed with water, and air
  9. customdried

Sources & evidence

ORD record
ord-e7c7ab45ba4f49a3a62cfbf648182e63
Source dataset
uspto-grants-1992_02
Patent number
US05087638

Reaction notes

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