Hydrochloric Acid → 4-Hydroxy-4'-octylazobenzene

HRID 1680983

Reaktionsgleichung

Reaktionsgleichung von HRID 1680983
[CH2:1]([C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl.[N:17]([O-])=O.[Na+].[OH-].[Na+].[C:23]1([OH:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[OH:29][C:23]1[CH:28]=[CH:27][C:26]([N:17]=[N:13][C:12]2[CH:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:15][CH:14]=2)=[CH:25][CH:24]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric Acid2×HCID 996PhenolHCID 14798Sodium HydroxideHCID 853464-OctylanilineHCID 23668193Sodium Nitrite

Produkt 1

HCID 27534414-Hydroxy-4'-octylazobenzeneAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

35 g (0.17 M) of 4-octylaniline was cooled to 0° C. or below, 85 g of 10% aqueous hydrochloride acid solution was added, and then a solution of 12.0 g of sodium nitrite in 68 ml of water was added. During the addition, the mixture was cooled so as not to exceed 0° C. After the addition, the mixture was allowed to react for 30 minutes, transferred into a dropping funnel and added dropwise into 170 g of an 8% NaOH aqueous solution containing 16 g of phenol held at 5° C. or below. After the addition, the mixture was stirred for 1 hour, and then 10% hydrochloric acid aqueous solution was added thereto until a pH of 5-6 to precipitate the reaction product. The precipitate was separated by filtration, washed with water, overnight under reduced pressure. After the drying, the product was washed with 500 ml of petroleum ether and further dried under reduced pressure to obtain 30.8 g (0.10 M) of 4-hydroxy-4'-octylazobenzene. The yield was 59%.

Aufarbeitung

  1. additionDuring the addition
  2. temperaturethe mixture was cooled so as not
  3. customto exceed 0° C
  4. additionAfter the addition
  5. customto react for 30 minutes
  6. customtransferred into a dropping funnel
  7. customheld at 5° C. or below
  8. additionAfter the addition
  9. customuntil a pH of 5-6 to precipitate the reaction product
  10. customThe precipitate was separated by filtration
  11. washwashed with water, overnight under reduced pressure
  12. washAfter the drying, the product was washed with 500 ml of petroleum ether
  13. customfurther dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4b99d2db8c994d2fbef3f30b237d8793
Quelldatensatz
uspto-grants-1992_12
Patentnummer
US05167857

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