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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 : |
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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]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; thionyl chloride;aluminium chloride; In dichloromethane; | Example 15 4,6-Dichloroindan-1-one (Not According to the Invention) Thionyl chloride (36.9 g) was added dropwise at 40 C. to a solution of 3-(2,4-di-chlorophenyl)propionic acid (43.8 g) in methylene chloride (200 ml). After reaction was complete, excess thionyl chloride and the solvent were removed by distillation. The oily residue was added dropwise at 40 C. to a suspension of aluminium chloride (53.3 g) in methylene chloride (200 ml). The reaction mixture was added to dilute hydrochloric acid after 18 hours at 40 C. The aqueous phase was separated off and extracted once with methylene chloride (250 ml). The combined organic phases were freed from the solvent. The residue was recrystallized from cyclohexane. 30 g of a colorless solid (m.p.: 115-116 C.) were obtained. | |
In PPA; hexane; water; | a 4,6-Dichloroindanone 3-(2,4-dichlorophenyl)propanoic acid (0.44 g, 2 mmol) in polyphosphoric acid (7 g) was heated to 100 C. under argon. After 90 min the mixture was cooled and treated with water (20 ml) and extracted with hexane (40 ml). The hexane layer was dried (MgSO4), and evaporated to dryness. The residue was purified by column chromatography on silica gel eluding with 0-30% dichloromethane in hexane to give the title product as a yellow solid, (0.018 g, 4.5%), deltaH (CDCl3) 2.8 (2H, m), 3.1 (2H, m), 7.6 (1H, d), 7.65 (1H, d). | |
12.2 g (55%) | 3b) 4,6-dichloro-1-indanone was prepared in a similar manner to that described in Example 1c from 3-(2,4-dichlorophenyl) propanoic acid (24.3 g, 0.11 mol). Chromatography on silica gel with hexanes:dichloromethane (1:1) as eluent gave 12.2 g (55%) of 4,6-dichloro-1-indanone as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Recrystallization of 1.0 g from hexanes gave 0.7 g of 4,6-dichloro-1-indanone as a white solid: mp 118-120 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10.6 g (65%) | 3c) Ethyl 2-(4,6-Dichloro-1-hydroxy-1-indanyl)acetate was prepared in a similar manner to that described in Example 1d from <strong>[52397-81-6]4,6-dichloro-1-indanone</strong>. Chromatography on silica gel with hexanes:ethyl acetate (8:2) as eluent gave 10.6 g (65%) of a yellow oil; NMR (CDCl)3): delta7.22-7.27 (m, 2H), 4.28 (br, 1H), 4.21 (m, 2H), 3.03 (m, 1H), 2.75 (m,3H), 2.30 (m, 2H), 1.28 (t, 3H). |
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