2-Chloro-4-Phenylphenol → 4-Octyl-4'-methoxy-3'-chlorobiphenyl

HRID 1390199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1390199
C1(C2C=CC(O)=C(Cl)C=2)C=CC=CC=1.C1(C2C=CC(OC)=C(Cl)C=2)C=CC=CC=1.[Cl-].C(O)CCCCCCC.[Cl-].[NH4+].[C:42]([C:51]1[CH:56]=[CH:55][C:54]([C:57]2[CH:62]=[CH:61][C:60]([O:63][CH3:64])=[C:59]([Cl:65])[CH:58]=2)=[CH:53][CH:52]=1)(=O)[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49]>C(=S)=S>[CH2:42]([C:51]1[CH:56]=[CH:55][C:54]([C:57]2[CH:62]=[CH:61][C:60]([O:63][CH3:64])=[C:59]([Cl:65])[CH:58]=2)=[CH:53][CH:52]=1)[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49]

Komponenten

7

Edukt 5

HCID 70742-Chloro-4-PhenylphenolHCID 25517Ammonium ChlorideHCID 6090921,1'-Biphenyl, 3-chloro-4-methoxy-HCID 233477224-Octanoyl-4'-methoxy-3'-chlorobiphenylHCID 23347723HCID 23347723, Verbindung

Produkt 1

HCID 204336094-Octyl-4'-methoxy-3'-chlorobiphenylAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6348Carbon DisulfideLösungsmittel

Versuchsvorschrift

4-phenyl-2-chlorophenol is methylated by means of well-known method steps and 4-phenyl-2-chloroanisole (hereinafter referred to as Material I) is extracted. 1/3 mole of Material I is dissolved into carbon disulfide 300cc and a Friedel Craft's reaction is effected in a MILO flask in which 1/3 mole of octanol chloride and 60 grams of anhydrous ammonium chloride are placed. As a result, 4-octanoyl-4'-methoxy-3'-chlorobiphenyl (hereinafter referred to as Compound 4) is extracted with a yield of 75%. As the result of reduction of said Compound 4, by the well-known Wolff-Kischner's reaction, 4-octyl-4'-methoxy-3'-chlorobiphenyl (hereinafter referred to as Compound 5) is extracted with a yield of 70 weight percent. 0.01 mole of 4-octyl-4'-hydroxy-3-chlorobiphenyl (hereinafter referred to as Material II), which is extracted from said Compound 5 by means of demethylation with HBr water, is dissolved into a mixed solution of 100cc pyridine and 50cc. of benzene. After this 0.012 mole of 4-octyloxy-benzoil chloride is added to the solution, this mixed solution is heated and stirred for 24 hours. Extraction is achieved by adding water (200cc) and benzene (100cc) to the solution. The resultant benzene layer is washed with a mixture of 1 mole of sodium hydroxide solution (50cc) and 1 mole of HCl liquid (100cc). The resultant compound in benzene layer is crystallized from ethyl alcohol (50cc). The result of the above method steps, 4-octyl-4'-(4"-octyloxy benzoil)-3'-chlorobiphenyl (Compound 1 in the above table), is extracted at the yield rate of 85%.

Aufarbeitung

  1. extractionis extracted
  2. customa Friedel Craft's reaction
  3. extractionis extracted with a yield of 75%

Quellen und Nachweise

ORD-Eintrag
ord-2ff377f3df1b4492b8ad37805de43f42
Quelldatensatz
uspto-grants-1979_02
Patentnummer
US04138359

Notizen zur Reaktion

Wird geladen…