Sulfuric Acid → 5-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one
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]2Participants
3
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
- temperatureunder reflux for 4 h
- customThe cooled reaction mixture
- extractionis cautiously extracted with ethyl acetate
- extractionthe organic extract
- extractionis extracted several times with saturated sodium bicarbonate solution
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customdried in vacuo
- 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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