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Formaldehyde → 2,4-Dibromo-6-[(tert-butylamino)methyl]phenol

HRID 1973184
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1973184
[CH2:1]=O.[C:3]([NH2:7])([CH3:6])([CH3:5])[CH3:4].[Br:8][C:9]1[CH:14]=[C:13]([Br:15])[CH:12]=[CH:11][C:10]=1[OH:16]>O1CCOCC1>[OH:16][C:10]1[C:9]([Br:8])=[CH:14][C:13]([Br:15])=[CH:12][C:11]=1[CH2:1][NH:7][C:3]([CH3:6])([CH3:5])[CH3:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 6385Tert-ButylamineHCID 120052,4-Dibromophenol

Produkt 1

HCID 5476212,4-Dibromo-6-[(tert-butylamino)methyl]phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
15 °C

Versuchsvorschrift

A mixture of 95 ml of 35% formaldehyde solution and 100 ml of dioxane is dropped into a solution of 80 g of tertiary butylamine in 350 ml of dioxane, cooled to 15° C, with stirring. The mixture is allowed to stand over night, then heated to 80° C. In the course of 4 hours a solution of 252 g of 2,4-dibromophenol in 250 ml of dioxane is dropped thereto, precipitating thereby the main charge of the reaction product. 1 hour after completion of this addition it is cooled, the precipitate is sucked off, washed with ethanol on the filter and dried. By concentrating the dioxane-mother liquor and the alcoholic washing liquid further material is obtained. Remaining reaction product precipitates from the dioxane concentrate in form of the hydrochloride by heating with alcoholic HCl. The hydrochloride is converted in H2O/CHCl3 in the free base with NaHCO3. Total yield = 268 g (79,5% of the theory). Recrystallization from acetic ester yields the N-(2-hydroxy-3,5-dibromobenzyl)-tert.butylamine in form of colorless felted needles, melting at 173°-175° C.

Aufarbeitung

  1. waitto stand over night
  2. temperatureheated to 80° C
  3. customprecipitating
  4. additionthe main charge of the reaction product
  5. addition1 hour after completion of this addition it
  6. temperatureis cooled
  7. washwashed with ethanol on the
  8. filtrationfilter
  9. customdried
  10. concentrationBy concentrating the dioxane-mother liquor
  11. washthe alcoholic washing liquid further material
  12. customis obtained
  13. customRemaining reaction product precipitates from the dioxane
  14. concentrationconcentrate in form of the hydrochloride
  15. temperatureby heating with alcoholic HCl
  16. customRecrystallization from acetic ester

Quellen und Nachweise

ORD-Eintrag
ord-cdf23870a0dc49edbf03c0380ef2f426
Quelldatensatz
uspto-grants-1976_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US03996279

Notizen zur Reaktion

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