Sulfuric Acid → HCID 20375429, compound

HRID 1448715Notes

Reaction equation

HRID 1448715 reaction equation
S(=O)(=O)(O)O.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14](O)[C:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[O:16])=[CH:10][CH:9]=1.[CH3:26][C:27]1[CH:28]=[C:29](O)[CH:30]=[CH:31][C:32]=1[CH3:33].[OH-].[Na+]>>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]2[O:16][C:30]3[CH:31]=[C:32]([CH3:33])[C:27]([CH3:26])=[CH:28][C:29]=3[C:14]=2[C:11]2[CH:12]=[CH:13][C:8]([O:7][CH3:6])=[CH:9][CH:10]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 72493,4-DimethylphenolHCID 14798Sodium HydroxideHCID 954154,4'-Dimethoxybenzoin

Product 1

HCID 20375429HCID 20375429, compound

Procedure

160 g of 73% strength aqueous sulphuric acid are added dropwise to a mixture of 54.5 g of 1,2-di-(4-methoxyphenyl)-2-oxo-ethanol (p-anisoin) and 73 g of 3,4-dimethylphenol and the mixture is heated at 130°-135° for 20 minutes and then cooled to 20°. The reaction mixture is rendered alkaline by adding an aqueous solution of sodium hydroxide and is heated under reflux and then cooled. It is extracted twice with ethyl acetate; the combined organic extracts are washed with a 2 N aqueous solution of sodium hydroxide and with water, dried over sodium sulphate and filtered and the filtrate is concentrated to half its volume and cooled. The crystalline precipitate is filtered off and recrystallised from ethyl acetate and gives 2,3-di-(4-methoxyphenyl)-5,6-dimethylbenzofurane, melting point 153°.

Workup

  1. temperaturethe mixture is heated at 130°-135° for 20 minutes
  2. temperaturecooled to 20°
  3. temperatureis heated
  4. temperatureunder reflux
  5. temperaturecooled
  6. extractionIt is extracted twice with ethyl acetate
  7. washthe combined organic extracts are washed with a 2 N aqueous solution of sodium hydroxide and with water
  8. dry with materialdried over sodium sulphate
  9. filtrationfiltered
  10. concentrationthe filtrate is concentrated to half its volume
  11. temperaturecooled
  12. filtrationThe crystalline precipitate is filtered off
  13. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-c45cd28e8b06426ea1409d93887947de
Source dataset
uspto-grants-1980_02
Patent number
US04187234

Reaction notes

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