Acetone → HCID 54382404, compound

HRID 1870628Notes

Reaction equation

HRID 1870628 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:10][C:9]2[C:4](=[C:5]([CH3:15])[C:6]([CH3:14])=[C:7]([CH:12]=O)[C:8]=2[CH3:11])[CH2:3]1.O.[OH-].[Na+].Cl.[CH3:21][C:22]([CH3:24])=[O:23]>>[CH3:1][C:2]1([CH3:16])[CH2:3][C:4]2[C:9](=[C:8]([CH3:11])[C:7]([CH3:12])=[C:6]([CH:14]=[CH:21][C:22](=[O:23])[CH3:24])[C:5]=2[CH3:15])[CH2:10]1

Participants

6

Reactant 5

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 137335152,2,4,6,7-Pentamethyl-2,3-dihydro-1H-indene-5-carbaldehyde

Product 1

HCID 54382404HCID 54382404, compoundYield 79%

Procedure

To a solution of 26.8 g of the 2,2,4,6,7-pentamethylindan-5-carboxaldehyde in 93 ml of absolute acetone was added 46 ml of water and 50 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 25.36 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-75c1ed6ca6f34057b0875df4a9532510
Source dataset
uspto-grants-2000_08
Patent number
US06096930

Reaction notes

Loading…