Acetone → HCID 54419997, compound

HRID 1870631Notes

Reaction equation

HRID 1870631 reaction equation
[CH2:1]([C:3]1([CH3:17])[CH2:11][C:10]2[C:5](=[C:6]([CH3:16])[C:7]([CH:14]=O)=[C:8]([CH3:13])[C:9]=2[CH3:12])[CH2:4]1)[CH3:2].O.[OH-].[Na+].Cl.[CH3:22][C:23]([CH3:25])=[O:24]>>[CH2:1]([C:3]1([CH3:17])[CH2:11][C:10]2[C:5](=[C:6]([CH3:16])[C:7]([CH:14]=[CH:22][C:23](=[O:24])[CH3:25])=[C:8]([CH3:13])[C:9]=2[CH3:12])[CH2:4]1)[CH3:2]

Participants

6

Reactant 5

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 18696672HCID 18696672, compound

Product 1

HCID 54419997HCID 54419997, compoundYield 79%

Procedure

To a solution of 18.26 g of the 2-ethyl-2,4,5,7-tetramethylindan-6-carboxaldehyde in 58 ml of absolute acetone was added 28 ml of water and 32 g of 2% NaOH. After refluxing for 20 hours, the solution was acidified was 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 19.38 g of the title compound as yellow 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-495ba5a8b9fb49f490591285d24db525
Source dataset
uspto-grants-2000_08
Patent number
US06096930

Reaction notes

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