Acetone → HCID 54437817, compound

HRID 1870639Notes

Reaction equation

HRID 1870639 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH2:6][C:7]([CH2:13][CH3:14])([CH3:12])[CH2:8]2)=[C:4]([CH3:15])[C:3]=1[CH:16]=O.O.[OH-].[Na+].Cl.[CH3:22][C:23]([CH3:25])=[O:24]>>[Cl:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH2:6][C:7]([CH2:13][CH3:14])([CH3:12])[CH2:8]2)=[C:4]([CH3:15])[C:3]=1[CH:16]=[CH:22][C:23](=[O:24])[CH3:25]

Participants

6

Reactant 5

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 18696710HCID 18696710, compound

Product 1

HCID 54437817HCID 54437817, compoundYield 78%

Procedure

To a solution of 24.35 g of the 6-chloro-2-ethyl-2,4,7-trimethylindan-5-carboxaldehyde in 73 ml of absolute acetone was added 36 ml of water and 40 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 22.08 g of the title compound as brown oil.

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-fc5e9071b41d4405819a8926d9f03ada
Source dataset
uspto-grants-2000_08
Patent number
US06096930

Reaction notes

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