Acetone → HCID 54357790, compound

HRID 1780604Notes

Reaction equation

HRID 1780604 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][C:8]([CH3:12])([CH3:11])[CH2:7][C:6]=2[C:5]([CH3:13])=[C:4]([CH3:14])[C:3]=1[CH:15]=O.O.[OH-].[Na+].[CH3:20][C:21]([CH3:23])=[O:22]>>[Cl:1][C:2]1[C:10]2[O:9][C:8]([CH3:11])([CH3:12])[CH2:7][C:6]=2[C:5]([CH3:13])=[C:4]([CH3:14])[C:3]=1[CH:15]=[CH:20][C:21](=[O:22])[CH3:23]

Participants

5

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 14798Sodium HydroxideHCID 19047071HCID 19047071, compound

Product 1

HCID 54357790HCID 54357790, compound

Conditions

Temperature
40 °C

Procedure

To a solution of 12 g of the 7-chloro-2,3-dihydro-2,2,4,5-tetramethyl-benzo-furan-6-carboxaldehyde in 25 ml of acetone was added 8 ml of water and 2 ml of 10% aqueous solution of sodium hydroxide. After refluxing at 40° C. for 15 hours, the reaction mixture was quenched with 2N aqueous solution of hydrochloric acid and the aqueous layer was extracted with diethyl ether. 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 silica-gel column chromatography to afford 10 g of 4-(7-chloro-2,3-dihydro-2,2,4,5-tetramethyl-benzofuran-6-yl)-3-buten-2-one

Workup

  1. customthe reaction mixture was quenched with 2N aqueous solution of hydrochloric acid
  2. extractionthe aqueous layer was extracted with diethyl ether
  3. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford a crude product
  7. customFinal purification

Sources & evidence

ORD record
ord-a141aeec220d4cb2933d453547771910
Source dataset
uspto-grants-1997_05
Patent number
US05631208

Reaction notes

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