p-Toluenesulfonic acid → 4-[1-(2-Hydroxyphenyl)ethylideneamino]-3-methylphenol
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].O[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O.C1(C)C=CC(S(O)(=O)=[O:27])=CC=1>O.C1(C)C=CC=CC=1>[OH:27][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:12](=[N:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9])[CH3:11]Participants
Procedure
To a 1 liter round bottom flask equipped with a water collector, water condenser, magnetic stirrer and drying tube was added 12.32 grams (0.10 mole) of 4-amino-3-methylphenol, 14.30 grams (0.105 mole) of 2-hydroxyacetophenone, 0.6 grams (0.005 moles) of p-toluenesulfonic acid and 500 milliliters of toluene. The resulting reaction mixture was stirred and refluxed for 100 hours during which time water was collected from the reaction. After the stirring and refluxing period, the reaction mixture was cooled to room temperature, filtered and left standing for 50 hours forming a solid material. The resulting solidified material was removed by filtration and recrystallized from toluene to give 10.10 grams (0.042 moles) of 4-[1-(2-hydroxyphenyl)ethylideneamino]-3-methylphenol having a melting point of 144°-156° C.
Workup
- customdrying tube
- customThe resulting reaction mixture
- customwas collected from the reaction
- temperatureAfter the stirring and refluxing period
- filtrationfiltered
- waitleft
- customforming a solid material
- customThe resulting solidified material was removed by filtration
- customrecrystallized from toluene
Sources & evidence
- ORD record
- ord-9187be5078a54c20b81b5f505e4a6cc6
- Source dataset
- uspto-grants-1983_08
- Patent number
- US04399148
Reaction notes
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