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Hydrochloric Acid → 2,4-Bis(1-methyl-1-phenylethyl)-6-[2-(2-nitrophenyl)diazenyl]phenol

HRID 1680615
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1680615
[OH-].[K+].[CH3:3][C:4]([C:12]1[CH:17]=[C:16]([C:18]([CH3:26])([CH3:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:15]=[CH:14][C:13]=1[OH:27])([CH3:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl-].[N+:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[N+:38]#[N:39])([O-:31])=[O:30].Cl>CO.C(O)(=O)C.O>[N+:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[N:38]=[N:39][C:14]1[CH:15]=[C:16]([C:18]([CH3:26])([CH3:25])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:17]=[C:12]([C:4]([CH3:3])([CH3:11])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:13]=1[OH:27])([O-:31])=[O:30]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 760132,4-DicumylphenolHCID 148932Benzenediazonium, 2-nitro-, chloride (1:1)

Produkt 1

HCID 1168102,4-Bis(1-methyl-1-phenylethyl)-6-[2-(2-nitrophenyl)diazenyl]phenol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176
Acetic Acid
Lösungsmittel
HCID 887MethanolLösungsmittel2×
HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
-4 °C

Versuchsvorschrift

To a 500-ml 3-necked flask fitted with a stirrer, thermometer, pressure equalized addition funnel and nitrogen inlets and outlets were charged 13.5 grams (0.21 mole) of potassium hydroxide pellets and 10 ml of water. The resulting hot solution was diluted with 80 ml of methanol. After flushing with nitrogen, 16.5 grams (0.05 mole) of 2,4-di-(α,α-dimethylbenzyl)phenol and 85 ml of methanol were added to give a clear solution which was then cooled to -4° C. A cold solution of o-nitrobenzenediazonium chloride in concentrated hydrochloric acid solution (42.9 grams=0.06 mole of diazonium solution) was added over a period of 15 minutes with rapid stirring while keeping the temperature between -2° and 0° C. The deep purple color of the azodye-phenoxide developed instantaneously as the diazonium solution was added. The resulting mixture was stirred for another 10 minutes at -1° to 1° C. The suspension was then acidified with 20 ml of glacial acetic acid over a 2-minute period at 1° to 3° C. The resulting brick red suspension was stirred for 15 minutes as the temperature was allowed to rise to ambient temperature and then filtered. The filter cake was washed with a cold solution of 40 grams ice in 160 ml of methanol and then with 1800 ml of water.

Aufarbeitung

  1. customTo a 500-ml 3-necked flask fitted with a stirrer
  2. additionaddition funnel and nitrogen inlets and outlets
  3. additionwere added
  4. customto give a clear solution which
  5. customthe temperature between -2° and 0° C
  6. additionwas added
  7. stirringThe resulting mixture was stirred for another 10 minutes at -1° to 1° C
  8. stirringThe resulting brick red suspension was stirred for 15 minutes as the temperature
  9. customto rise to ambient temperature
  10. filtrationfiltered
  11. washThe filter cake was washed with a cold solution of 40 grams ice in 160 ml of methanol

Quellen und Nachweise

ORD-Eintrag
ord-e70e189e6eb4468f997e5be87a5e665b
Quelldatensatz
uspto-grants-1981_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04275004

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