Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 54276481 | HCID 54276481 | — |
| Catalyst | Iron | HCID 23925 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 53674338 | HCID 53674338 | 73.5% |
Reaction Steps
21.22 g of 1,4-bis[4-(4-nitrophenyl)-1,3-butadienyl]benzene was put into 800 ml of dimethylformamide (DMF). To this mixture, 33.51 g of iron powder and an aqueous solution of hydrochloric acid prepared by diluting 8.5 ml of concentrated hydrochloric acid with 28 ml of water were successively added with stirring, and the obtained mixture was further stirred at 95 to 102° C. for 4 hours. The resultant mixture was cooled to 90° C., and adjusted to pH 9 by the addition of a 40% aqueous solution of sodium hydroxide. Thereafter, the insoluble matter was removed from the mixture by filtration using Celite™. The filtrate was concentrated to about 400 ml under reduced pressure. With the addition of 20 ml of water, the concentrated filtrate was cooled to room temperature. The separating crystals were collected by filtration, and successively washed with water and methanol, and heated with the application of heat under reduced pressure, whereby 13.40 g of mud yellow crystals was obtained in a 73.5% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06448384B1 |
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| Source dataset | uspto-grants-2002_09 |
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| ORD ID | ord-7dee3b97730540eeb80afcd0ce79084d |
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| Source note | uspto-grants-2002_09 |
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