P-Toluenesulfonamide → 3-Methoxy-4-methylbenzonitrile
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:6](O)=O.C1(C)C=CC(S([NH2:22])(=O)=O)=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]#[N:22])[CH:9]=[CH:10][C:11]=1[CH3:12]Participants
Conditions
- Temperature
- 200 °C
Procedure
A mixture of 49 grams (295 millimoles) of 3-methoxy-4-methylbenzoic acid, 53.9 grams (315 millimoles) of p-toluene-sulfonamide, and 129 grams (619 millimoles) of phosphorus pentachloride was prepared and then heated at 200° C. while stirring. Phosphorus oxychloride was distilled at 106°-112° C.; and the mixture was further heated at 200° C. while stirring until no distillated came out. To the reaction mixture was added while stirring and cooling with ice 120 milliliters of pyridine in small portions and further 550 milliliters of water. Crystals precipitated were separated by filtration, suspended in 200 milliliters of a 5% aqueous sodium hydroxide solution, and then stirred at room temperature for 30 minutes. These crystals were separated by filtration and the crude product thus obtained was purified by steam distillation to obtain 36.5 grams of 3-methoxy-4-methylcyano-benzene (yield, 84%).
Workup
- customwas prepared
- distillationPhosphorus oxychloride was distilled at 106°-112° C.
- temperatureand the mixture was further heated at 200° C.
- stirringwhile stirring until
- additionTo the reaction mixture was added
- stirringwhile stirring
- temperaturecooling with ice 120 milliliters of pyridine in small portions and further 550 milliliters of water
- customCrystals precipitated
- customwere separated by filtration
- stirringstirred at room temperature for 30 minutes
- customThese crystals were separated by filtration
- customthe crude product thus obtained
- distillationwas purified by steam distillation
Sources & evidence
- ORD record
- ord-500569309a264560a5fdbf65c150fc3d
- Source dataset
- uspto-grants-1987_07
- Patent number
- US04680054
Reaction notes
Loading…