Methanol → 3-(Phenylethynyl)aniline

HRID 846832

Reaktionsgleichung

Reaktionsgleichung von HRID 846832
[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[C:11]([N+:15]([O-])=O)[CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].CO>O>[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=2)[NH2:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 73972Sodium sulfide nonahydrateHCID 800027Stk331085

Produkt 1

HCID 134317733-(Phenylethynyl)anilineAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a 5-liter multi-necked flask fitted with a mechanical stirrer, reflux condenser, and thermometer was charged 215.6 g (0.96 mol) of 3-phenylethynylnitrobenzene obtained as described above, 600.2 g (2.5 mol) of sodium sulfide nonahydrate, 2 liters of methanol, and 500 ml of distilled water. The system is brought to 70° C. for 3 hours at which point the reduction is complete by thin layer chromatography. The reaction mixture is cooled to room temperature and the methanol removed by a rotary evaporator. The concentrate is added to a separatory funnel along with 1 liter of toluene. The toluene layer is separated and washed with distilled water until neutral to pH paper. Concentration of the toluene solution followed by vacuum distillation gave 131 g (0.68 mol, 71% yield) of 3-phenylethynylaniline.

Aufarbeitung

  1. customTo a 5-liter multi-necked flask fitted with a mechanical stirrer
  2. temperaturereflux condenser
  3. customobtained
  4. customthe methanol removed by a rotary evaporator
  5. additionThe concentrate is added to a separatory funnel along with 1 liter of toluene
  6. customThe toluene layer is separated
  7. washwashed with distilled water until neutral
  8. distillationConcentration of the toluene solution followed by vacuum distillation

Quellen und Nachweise

ORD-Eintrag
ord-c9fb7441fe7745b88bb84344fcc952e1
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05138028

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