Acetone → HCID 53953563, compound

HRID 1780616Notes

Reaction equation

HRID 1780616 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:6][C:5]2[C:7]([CH3:15])=[C:8]([CH3:14])[C:9]([CH:12]=O)=[C:10]([CH3:11])[C:4]=2[O:3]1.O.[OH-].[Na+].[CH3:20][C:21]([CH3:23])=[O:22]>>[CH3:1][C:2]1([CH3:16])[CH2:6][C:5]2[C:7]([CH3:15])=[C:8]([CH3:14])[C:9]([CH:12]=[CH:20][C:21](=[O:22])[CH3:23])=[C:10]([CH3:11])[C:4]=2[O:3]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 14798Sodium HydroxideHCID 19047057HCID 19047057, compound

Product 1

HCID 53953563HCID 53953563, compound

Procedure

To a solution of 37 g of the 2,3-dihydro-2,2,4,5,7-pentamethylbenzofuran-6-carboxaldehyde in 125 ml of acetone was added 60 ml of water and 68 g of 2% aqueous solution of sodium hydroxide. After refluxing for 20 hours, the reaction mixture was quenched with 10 ml of 2N aqueous solution of hydrochloric acid and the aqueous layer was extracted with dichloromethane. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford a crude product. Final purification was carried by recrystallization to afford 42.4 g of 4-(2,3-dihydro-2,2,4,5,7-pentamethylbenzofuran-6-yl)-3-butene-2-one.

Workup

  1. temperatureAfter refluxing for 20 hours
  2. customthe reaction mixture was quenched with 10 ml of 2N aqueous solution of hydrochloric acid
  3. extractionthe aqueous layer was extracted with dichloromethane
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford a crude product
  8. customFinal purification
  9. customwas carried by recrystallization

Sources & evidence

ORD record
ord-0eab6b6418f7496e95006dd1a7383653
Source dataset
uspto-grants-1997_05
Patent number
US05631208

Reaction notes

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