Water → 4-Methyl-3-nitrobenzyl alcohol

HRID 386734

Reaktionsgleichung

Reaktionsgleichung von HRID 386734
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].O.[BH4-].[Na+]>O1CCOCC1>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Komponenten

5

Edukt 3

HCID 962WaterHCID 663234-Methyl-3-nitrobenzoyl chlorideHCID 4311764Sodium borohydride

Produkt 1

HCID 1234974-Methyl-3-nitrobenzyl alcoholAusbeute 86,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

A solution of 4-methyl-3-nitrobenzoylchloride (5.5 g) in dioxane (30 mL) was added dropwise to a solution of water (30 mL), dioxane (30 mL) and sodium borohydride (2.5 g) under ice cooling. The reaction solution was refluxed for one hour, and after cooling, the solution was filtered through Celite. Water was added to the filtrate, the mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a crude product of (4-methyl-3-nitrophenyl)methanol (4 g).

Aufarbeitung

  1. temperatureThe reaction solution was refluxed for one hour
  2. temperatureafter cooling
  3. filtrationthe solution was filtered through Celite
  4. additionWater was added to the filtrate
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4ffd6bfc4ee44fbcaebba2c1619bb97e
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372867B2

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