Bromomethyl 4-methoxyphenyl ketone → 2-(p-Methoxybenzoyl)-3-methyl-4-hydroxybenzofuran

HRID 1607271Notes

Reaction equation

HRID 1607271 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.C(=O)([O-])[O-].[K+].[K+].[CH3:18][O:19][C:20]1[CH:29]=[CH:28][C:23]([C:24](=[O:27])[CH2:25]Br)=[CH:22][CH:21]=1>CC(C)=O>[CH3:18][O:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([C:25]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:27])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 11430Potassium CarbonateHCID 696872',6'-Dihydroxyacetophenone

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 1N 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 1N sodium hydroxide
  7. filtrationThe solid was filtered
  8. washwashed with water
  9. customair-dried

Sources & evidence

ORD record
ord-7f637a2c491744ee9031df37d50cf7d0
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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