Hydrochloric Acid → [1,1'-Biphenyl]-3-methanol, 2-methyl-

HRID 1065556

Reaktionsgleichung

Reaktionsgleichung von HRID 1065556
[CH3:1][C:2]1[C:9]([N+:10]([O-])=O)=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[ClH:13].[OH-].[K+]>[Fe].C(O)C>[CH3:1][C:2]1[C:3]([CH2:4][OH:5])=[CH:6][CH:7]=[CH:8][C:9]=1[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:3]=1.[ClH:13].[OH:5][CH2:4][C:3]1[C:2]([CH3:1])=[C:9]([CH:8]=[CH:7][CH:6]=1)[NH2:10]

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 902892-Methyl-3-nitrobenzyl alcohol

Produkt 2

HCID 596875[1,1'-Biphenyl]-3-methanol, 2-methyl-HCID 20270659(3-Amino-2-methylphenyl)methanol hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

2-Methyl[1,1'-biphenyl]-3-methanol was prepared as follows: To 100 ml of stirred 50% aqueous ethanol was added 2-methyl-3-nitrobenzyl alcohol (41.8 g, 0.25 mole) and 85.0 grams of iron powder. The mixture was brought to reflux, and 5.2 ml of concentrated hydrochloric acid was slowly added. Upon complete addition, the reaction mixture was stirred under reflux for 2 hours. The reaction mixture was then made just basic with ethanolic 15% potassium hydroxide. The hot mixture was filtered through diactomaceous earth to remove the iron. The filter cake was washed with ethanol. The filtrate was acidified with hydrogen chloride, then allowed to stand at room temperature for 16 hours. The ethanol was removed by evaporation under reduced pressure. Hexane was added to the residue, and the water-hexane azeotrope was removed by distillation. The addition of hexane and the subsequent removal of the water-hexane azeotrope by distillation was repeated three times. The 3-hydroxymethyl-2-methylaniline hydrochloride residue thus obtained was used as follows.

Aufarbeitung

  1. temperatureto reflux
  2. additionUpon complete addition
  3. temperatureunder reflux for 2 hours
  4. filtrationThe hot mixture was filtered through diactomaceous earth
  5. customto remove the iron
  6. washThe filter cake was washed with ethanol
  7. customThe ethanol was removed by evaporation under reduced pressure
  8. additionHexane was added to the residue
  9. customthe water-hexane azeotrope was removed by distillation
  10. additionThe addition of hexane
  11. customthe subsequent removal of the water-hexane azeotrope
  12. distillationby distillation

Quellen und Nachweise

ORD-Eintrag
ord-d86913fc311c4f90af08a9f9532b4fa1
Quelldatensatz
uspto-grants-1982_05
Patentnummer
US04329518

Verknüpfte Notizen

Wird geladen…