Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Dimethyl oxalate | HCID 11120 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 1-(4-Chloro-2-methoxyphenyl)ethan-1-one | HCID 19429468 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68641713 | HCID 68641713 | 54% |
Reaction Steps
To dimethylformamide (13 ml), 1-(4-chloro-2-methoxyphenyl)ethanone (3.13 g) and dimethyl oxalate (2.4 g) were added, and 60% sodium hydride suspension in oil (811 mg) was added thereto at 0° C. The mixture was stirred at a room temperature for one hour, and then heated to 50° C. and stirred for 19 hours. The mixture was allowed to cool to a room temperature, 3-N hydrochloric acid was added to the mixture. The resulting mixture was subjected to extraction with ethyl acetate. The organic layer was washed with water and a saturated saline solution in order, then dried over anhydrous magnesium sulfate, and concentrated under a reduced pressure. In the process of the concentration, the precipitated crystal was separated by filtration to give the title compound (2.47 g, 54%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09200008B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-087c47f10cdc4986a67d3386de5daf13 |
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| Source note | uspto-grants-2015_12 |
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