Sulfuric Acid → 5-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one

HRID 1977822Notes

Reaction equation

HRID 1977822 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=NN(C)C)[CH:6]([CH3:15])[CH2:5]2.S(=O)(=O)(O)[OH:17]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:17])[CH:6]([CH3:15])[CH2:5]2

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 57141471HCID 57141471, compound

Product 1

HCID 219956145-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one

Procedure

5.5 g of N′-(5-chloro-2-methylindan-1-ylidene)-N,N-dimethylhydrazine are emulsified in 100 ml of 2N sulfuric acid and boiled under reflux for 4 h. The cooled reaction mixture is cautiously extracted with ethyl acetate; the organic extract is extracted several times with saturated sodium bicarbonate solution, dried over sodium sulfate, filtered, dried in vacuo and chromatographed on silica gel with ethyl acetate/hetpane ⅕. 5-Chloro-2-methylindan-1-one is obtained as an oil.

Workup

  1. temperatureunder reflux for 4 h
  2. customThe cooled reaction mixture
  3. extractionis cautiously extracted with ethyl acetate
  4. extractionthe organic extract
  5. extractionis extracted several times with saturated sodium bicarbonate solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customdried in vacuo
  9. customchromatographed on silica gel with ethyl acetate/hetpane ⅕

Sources & evidence

ORD record
ord-337d1f1bf71d47848e6fc5498f9b138b
Source dataset
uspto-grants-2001_05
Patent number
US06235763B1

Reaction notes

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