Potassium Hydroxide → 3-(m-Phenoxyphenoxy)-3'-(o-phenoxyphenoxy)biphenyl

HRID 1076463

반응식

HRID 1076463 반응식
[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl[C:18]1[CH:19]=[C:20]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([O:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH:32]=3)[CH:25]=2)[CH:21]=[CH:22][CH:23]=1>[Cu].C1(C)C=CC=CC=1>[O:37]([C:33]1[CH:32]=[C:31]([CH:36]=[CH:35][CH:34]=1)[O:30][C:26]1[CH:25]=[C:24]([C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([O:14][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:19]=2)[CH:29]=[CH:28][CH:27]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

참가 물질

6

반응물 3

HCID 14797Potassium HydroxideHCID 754912-Hydroxydiphenyl etherHCID 215369223-Chloro-3'-(m-phenoxyphenoxy)biphenyl

생성물 1

HCID 215369303-(m-Phenoxyphenoxy)-3'-(o-phenoxyphenoxy)biphenyl수율 61%

시약·촉매·용매 2

HCID 23978Copper촉매HCID 1140Toluene용매

실험 절차

A 500 ml. reaction flask equipped with stirrer, condenser, and Dean Stark trap was charged with 191 g. (1.03 moles) of o-phenoxyphenol, 50 ml. of toluene and 39.5 g. (0.70 mole) of potassium hydroxide. The mixture was heated to reflux and water azeotroped from the system. Diglyme (100 ml.) was then added followed by 20 g. (0.053 mole) of 3-chloro-3'-(m-phenoxyphenoxy)biphenyl over a 30 minute period. To this mixture 2.5 g. of cuprous chloride and 0.5 g. of copper powder was added and after removing the diglyme be distillation, the reaction mixture was heated at 230°-240° for 18 hours. The mixture was cooled, diluted with 500 ml. of ether and centrifuged to remove copper and potassium salts. The salts were washed with additional ether, and the ether fractions combined and washed with 25% potassium hydroxide solution followed by water washing to neutrality. After drying the ethereal solution over magnesium sulfate, and removing ether in vacuo, the resulting oil was distilled to give 16.9 g of the desired product, bp 255°-260°/0.02 mm.; nD25 1.6480.

후처리

  1. customreaction flask
  2. customequipped with stirrer, condenser
  3. additionDean Stark trap was charged with 191 g
  4. temperatureThe mixture was heated
  5. temperatureto reflux
  6. customwater azeotroped from the system
  7. additionDiglyme (100 ml.) was then added
  8. customafter removing the diglyme
  9. distillationdistillation
  10. temperaturethe reaction mixture was heated at 230°-240° for 18 hours
  11. temperatureThe mixture was cooled
  12. additiondiluted with 500 ml
  13. customto remove copper and potassium salts
  14. washThe salts were washed with additional ether
  15. washwashed with 25% potassium hydroxide solution
  16. dry with materialAfter drying the ethereal solution over magnesium sulfate
  17. customremoving ether in vacuo
  18. distillationthe resulting oil was distilled

출처 및 근거

ORD 기록
ord-95bad390f76a4b19915d1471fd4e2366
출처 데이터셋
uspto-grants-1976_05
특허 번호
US03957666

연결된 노트

불러오는 중…