Acetone → HCID 53978158, compound

HRID 1870634Notes

Reaction equation

HRID 1870634 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH2:6][C:7]([CH3:13])([CH3:12])[CH2:8]2)=[C:4]([CH3:14])[C:3]=1[CH:15]=O.O.[OH-].[Na+].Cl.[CH3:21][C:22]([CH3:24])=[O:23]>>[Cl:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH2:6][C:7]([CH3:12])([CH3:13])[CH2:8]2)=[C:4]([CH3:14])[C:3]=1[CH:15]=[CH:21][C:22](=[O:23])[CH3:24]

Participants

6

Reactant 5

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 18696675HCID 18696675, compound

Product 1

HCID 53978158HCID 53978158, compoundYield 65%

Procedure

To a solution of 21.8 g of the 6-chloro-2,2,4,7-tetramethylindan-5-carboxaldehyde in 67 ml of absolute acetone was added 33 ml of water and 36.5 g of 2% NaOH. After refluxing for 20 hours, the solution was acidified with 2N HCl and extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by silica-gel column chromatography to afford 16.6 g of the title compound as yellow solid.

Workup

  1. temperatureAfter refluxing for 20 hours
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-9fbabc9e67564fe0a716b5536788a78e
Source dataset
uspto-grants-2000_08
Patent number
US06096930

Reaction notes

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