Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Benzoylacetone | HCID 7166 | — |
| Reactant | 2-Nitrobenzoyl chloride | HCID 11875 | — |
| Reactant | Magnesium ethanolate | HCID 164963 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 14403266 | HCID 14403266 | 73.2% |
Reaction Steps
A mixture of benzoylacetone (8.1 g, 0.05 mole), magnesium ethoxide (5.7 g, 0.05 mole) and ethyl ether (100 ml) was heated at reflux for 1 hour. The reaction mixture was cooled to room temperature, and 2-nitrobenzoyl chloride (11.1 g, 0.06 mole) was added dropwise over a period of 15 minutes. The reaction mixture was then heated at reflux for 1 hour. After cooling to room temperature, the reaction mixture was poured into 50 ml of 2N hydrochloric acid, and the phases separated. The ether layer was extracted with 5% potassium carbonate. The basic extract was acidified with hydrochloric acid and extracted with ether. The ether extract was washed with saturated sodium chloride, dried over magnesium sulfate and concentrated under vacuum yielding 11.4 g of the desired product as a white solid with a melting point of 99°-103° C. It was identified as such by nuclear magneticresonance spectroscopy, infrared spectroscopy and mass spectroscopy.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US04795489 |
|---|
| Source dataset | uspto-grants-1989_01 |
|---|
| ORD ID | ord-915cb3a9c0664bc58af3ccf1a2398e2c |
|---|
| Source note | uspto-grants-1989_01 |
|---|