Hydrochloric Acid → (2,6-Dimethyl-3-nitrophenyl)methyl acetate

HRID 485542

Reaktionsgleichung

Reaktionsgleichung von HRID 485542
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH3:11])[C:3]=1[CH2:12][OH:13].N1C=CC=CC=1.[C:20](Cl)(=[O:22])[CH3:21].Cl>C1(C)C=CC=CC=1>[C:20]([O:13][CH2:12][C:3]1[C:4]([CH3:11])=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[CH3:1])(=[O:22])[CH3:21]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 10487641(2,6-Dimethyl-3-nitrophenyl)methanol

Produkt 1

HCID 10537042(2,6-Dimethyl-3-nitrophenyl)methyl acetateAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A stirred solution of 2,6-dimethyl-3-nitrobenzene-1-methanol (51.3 g, 0.283 mole) and 25 ml of pyridine in 350 ml of toluene was warmed to 70°. During a ten minute period, acetyl chloride (22.2 g, 0.283 mole) was added to the reaction mixture. The reaction mixture was heated at 85° for 21/2 hours, then poured over 300 g of ice, and 100 ml of a 4N hydrochloric acid solution was added thereto. The organic phase was separated and washed with 100 ml of aqueous 2N hydrochloric acid, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed from the filtrate under reduced pressure to give (2,6-dimethyl-3-nitrophenyl)methyl acetate (47.5 g) as an oil.

Aufarbeitung

  1. temperatureThe reaction mixture was heated at 85° for 21/2 hours
  2. additionwas added
  3. customThe organic phase was separated
  4. washwashed with 100 ml of aqueous 2N hydrochloric acid
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed from the filtrate under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e9f4779c1f8445f39d18d58bb748ebf3
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04536591

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