Methanol → (2,6-Dimethyl-3-nitrophenyl)methanol

HRID 354535

Reaktionsgleichung

Reaktionsgleichung von HRID 354535
CC1C=CC=C(C)C=1C(O)=O.[CH3:12][C:13]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18]([CH3:25])[C:14]=1[C:15]([OH:17])=[O:16].CO>O1CCCC1>[CH3:12][C:13]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18]([CH3:25])[C:14]=1[C:15]([OH:17])=[O:16].[CH3:12][C:13]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18]([CH3:25])[C:14]=1[CH2:15][OH:16]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 124392,6-Dimethylbenzoic acidHCID 2393292,6-Dimethyl-3-nitrobenzoic acid

Produkt 2

HCID 2393292,6-Dimethyl-3-nitrobenzoic acidHCID 10487641(2,6-Dimethyl-3-nitrophenyl)methanolAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2,6-Dimethyl-3-nitrobenzoic acid was prepared by nitrating 2,6-dimethylbenzoic acid. A solution of 2,6-dimethyl-3-nitrobenzoic acid (30 grams, 0.15 mole) in tetrahydrofuran (100 ml) was stirred under nitrogen. Borane-methyl sulfide complex (20 ml, 0.2 mole) was added dropwise at room temperature. When one fourth of the borane complex had been added the reaction mixture was brought to reflux. Reflux continued for one hour after complete addition of the borane complex. The reaction mixture was cooled to 0°, and cold methanol (500 ml) was added dropwise until foaming ceased and then added rapidly. The solvent was evaporated, and the crude product was dissolved in methylene chloride and washed with 2 N sodium hydroxide. The solvent was removed by evaporation to give (2,6-dimethyl-3-nitrophenyl)methanol (12.0 grams; mp 84°-92°).

Aufarbeitung

  1. additionBorane-methyl sulfide complex (20 ml, 0.2 mole) was added dropwise at room temperature
  2. additionWhen one fourth of the borane complex had been added the reaction mixture
  3. temperatureto reflux
  4. temperatureReflux
  5. additionafter complete addition of the borane complex
  6. temperatureThe reaction mixture was cooled to 0°
  7. additionadded rapidly
  8. customThe solvent was evaporated
  9. dissolutionthe crude product was dissolved in methylene chloride
  10. washwashed with 2 N sodium hydroxide
  11. customThe solvent was removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-de9954a06a1e436db4426b380dac932f
Quelldatensatz
uspto-grants-1983_03
Patentnummer
US04375476

Verknüpfte Notizen

Wird geladen…