Acetone → HCID 53818303, compound

HRID 1870645Notes

Reaction equation

HRID 1870645 reaction equation
[Cl:1][C:2]1[C:3]([CH:15]=O)=[C:4]([CH3:14])[C:5]([CH3:13])=[C:6]2[C:10]=1[CH2:9][C:8]([CH3:12])([CH3:11])[CH2:7]2.O.[OH-].[Na+].Cl.[CH3:21][C:22]([CH3:24])=[O:23]>>[Cl:1][C:2]1[C:3]([CH:15]=[CH:21][C:22](=[O:23])[CH3:24])=[C:4]([CH3:14])[C:5]([CH3:13])=[C:6]2[C:10]=1[CH2:9][C:8]([CH3:11])([CH3:12])[CH2:7]2

Participants

6

Reactant 5

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 18696703HCID 18696703, compound

Product 1

HCID 53818303HCID 53818303, compoundYield 35%

Procedure

To a solution of 14.7 g of the 7-chloro-2,2,4,5-tetramethylindan-6-carboxaldehyde in 48 ml of absolute acetone was added 23 ml of water and 25 g of 2% NaOH. After refluxing for 20 hours the solution was acidified with 2N HCl 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 5.35 g of the title compound as yellow solid.

Workup

  1. temperatureAfter refluxing for 20 hours the solution
  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-5c688e3091d44979a7ba7507fdb5922e
Source dataset
uspto-grants-2000_08
Patent number
US06096930

Reaction notes

Loading…