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CAS No. : | 52397-81-6 | MDL No. : | MFCD08276785 |
Formula : | C9H6Cl2O | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | BIGNWTAXBIQGAZ-UHFFFAOYSA-N |
M.W : | 201.05 | Pubchem ID : | 12206518 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With aluminum (III) chloride; In dichloromethane; at 20℃; for 3.0h;Inert atmosphere; Reflux; | Oxalyl chloride (6.9 g, 55 mmol) was added dropwise at room temperature to a solution of 3-(2,4-dichlorophenyl)propanoic acid (7, 11 g, 50 mmol) in 20 ml of dichloromethane. The mixture was stirred for 2 h at room temperature, then the excess oxalyl chloride was removed in vacuo to give 3-(2,4-dichlorophenyl)propanoyl chloride, which was dissolved in 50 ml of dichloromethane. This solution was added dropwise at room temperature to amixture of aluminium chloride (7.3 g, 55 mmol) in 50 ml dichloromethane.Subsequently the reaction mixture was heated for 3 h to reflux, cooled to room temperature again and poured on ice-water. After separation of the phases, the organic layer was washed with saturated aqueous sodium bicarbonate solution and water, dried over sodium sulfate and concentrated under reduced pressure. The remainder was purified by chromatography on silica gel, using hexane /dichloromethane 1 : 1 as eluent system to deliver 4,6-dichloroindan-1-one (8, 5.4g, 27 mmol, 55 %). 1H-NMR (400 MHz, CDCl3): delta = 2.69 (t, 2H, J = 5.7 Hz),3.05 (t, 2H, J = 5.7 Hz), 7.63 (d, 1H, J = 2.0 Hz), 7.94 (d, 1H, J = 2.0 Hz). LC-MS:Rt = 1.02 min; MS: m/z = 201 [M+1]+. |
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