Hydrochloric Acid → 3-Chlorobiphenyl

HRID 1390200

반응식

HRID 1390200 반응식
C([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18](O)=[CH:17][CH:16]=2)=[CH:11][C:10]=1[Cl:22])CCCCCCC.C(C1C=CC(C2C=CC(OC)=C(Cl)C=2)=CC=1)CCCCCCC.[OH-].[Na+].Cl>>[Cl:22][C:10]1[CH:11]=[C:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:13]=[CH:14][CH:9]=1

참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20433609HCID 20433609, 화합물HCID 23347720HCID 23347720, 화합물

생성물 1

HCID 163223-Chlorobiphenyl

실험 절차

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%.

후처리

  1. extractionis extracted with a yield of 70 weight percent
  2. extractionis extracted
  3. dissolutionis dissolved into a mixed solution of 100cc pyridine and 50cc
  4. temperaturethis mixed solution is heated
  5. extractionExtraction
  6. additionby adding water (200cc) and benzene (100cc) to the solution
  7. customThe resultant compound in benzene layer is crystallized from ethyl alcohol (50cc)

출처 및 근거

ORD 기록
ord-1f8b4dba48ba4f39a6a1494a17a277dc
출처 데이터셋
uspto-grants-1979_02
특허 번호
US04138359

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