Acetone → HCID 54552323, compound

HRID 1870648Notes

Reaction equation

HRID 1870648 reaction equation
[Cl:1][C:2]1[C:3]([CH:16]=O)=[C:4]([CH3:15])[C:5]([CH3:14])=[C:6]2[C:10]=1[CH2:9][C:8]([CH2:12][CH3:13])([CH3:11])[CH2:7]2.O.[OH-].[Na+].Cl.[CH3:22][C:23]([CH3:25])=[O:24]>>[Cl:1][C:2]1[C:3]([CH:16]=[CH:22][C:23](=[O:24])[CH3:25])=[C:4]([CH3:15])[C:5]([CH3:14])=[C:6]2[C:10]=1[CH2:9][C:8]([CH2:12][CH3:13])([CH3:11])[CH2:7]2

Participants

6

Reactant 5

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 18696669HCID 18696669, compound

Product 1

HCID 54552323HCID 54552323, compoundYield 73.7%

Procedure

To a solution of 14.7 g of the 7-chloro-2-ethyl-2,4,5-trimethylindan-6-carboxaldehyde in 45 ml of absolute acetone was added 22 ml of water and 24 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 12.65 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-b1c084a505864bc5941f9a4d8a71e94a
Source dataset
uspto-grants-2000_08
Patent number
US06096930

Reaction notes

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