HuagongsheHuagongshe Chemistry Print Report · For research reference only
p-Toluenesulfonic acid → N-(4-Methoxybenzyl)-4-chloro-2-(trifluoroacetyl)aniline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | 4-Methoxybenzyl alcohol | HCID 7738 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 1-(2-Amino-5-chlorophenyl)-2,2,2-trifluoroethan-1-one--hydrogen chloride--water (1/1/1) | HCID 44181989 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Toluene water | HCID 22272177 | — |
| Product | N-(4-Methoxybenzyl)-4-chloro-2-(trifluoroacetyl)aniline | HCID 11089189 | — |
Reaction Steps
To a slurry of 4-Chloro-2-trifluoroacetylaniline, hydrochloride hydrate (40.0 kg, 144 mol) in toluene (140 kg) and water (50 L) was added 30% NaOH (18 kg) to pH 7.0. After removing the aqueous phase, 4-methoxybenzyl alcohol (20 kg, 144 mol) and TsOH (1.0 kg, 5.3 mol) were added. The solution was heated to reflux and the water/toluene azeotrope (30 L) distilled. The solution was cooled to room temperature and washed with saturated brine (80 kg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05925789 |
| Source dataset | uspto-grants-1999_07 |
| ORD ID | ord-53e2aeaf45e64eed9bccc53778c8ab99 |
| Source note | uspto-grants-1999_07 |