Potassium Hydroxide → 3-(m-Phenoxyphenoxy)-3'-[m-(m-phenoxyphenoxy)phenoxy]biphenyl

HRID 1076465Notes

Reaction equation

HRID 1076465 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:19]=[CH:20][CH:21]=1)[O:11][C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].ClC1C=C([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([O:37][C:38]3[CH:43]=[CH:42][CH:41]=[C:40]([O:44][C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[CH:39]=3)[CH:32]=2)C=CC=1>[Cu].C1(C)C=CC=CC=1>[O:37]([C:38]1[CH:39]=[C:40]([CH:41]=[CH:42][CH:43]=1)[O:44][C:45]1[CH:50]=[C:49]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([O:1][C:8]3[CH:21]=[CH:20][CH:19]=[C:10]([O:11][C:12]4[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)[CH:13]=4)[CH:9]=3)[CH:3]=2)[CH:48]=[CH:47][CH:46]=1)[C:33]1[CH:32]=[CH:31][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 84251Phenol, 3-(3-phenoxyphenoxy)-HCID 215369223-Chloro-3'-(m-phenoxyphenoxy)biphenyl

Product 1

HCID 215369583-(m-Phenoxyphenoxy)-3'-[m-(m-phenoxyphenoxy)phenoxy]biphenyl

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1140TolueneSolvent

Procedure

A 500 ml. reaction flask equipped with stirrer, condenser and Dean-Stark trap was charged with 59.8 g. (0.215 mole) of m-(m-phenoxyphenoxy)phenol, 50 ml. of toluene and 7.2 g. (0.129 mole) of potassium hydroxide. Water was azeotroped from the system and 100 ml. of diglyme added followed by dropwise addition of 20 g. (0.053 mole) of 3-chloro-3'-(m-phenoxyphenoxy)biphenyl over a 30 min. period. To this mixture 2.5 g. of cuprous chloride and 0.5 g. of copper powder was added. Diglyme was distilled from the system and the resulting mixture heated at 230°-240°C. for 18 hours. At the end of this time, 250 ml. of ether was added to the cooled mixture and the resulting slurry centrifuged to remove salts. The ethereal solution was washed thoroughly with aqueous base, water and then dried over anhydrous magnesium sulfate. The ether was removed under vacuum, and the resulting oil was distilled to give 24.4 g. of the desired product, bp 340°/ 0.05 mm., nD25 1.6510.

Workup

  1. customreaction flask
  2. customequipped with stirrer, condenser
  3. additionDean-Stark trap was charged with 59.8 g
  4. customWater was azeotroped from the system and 100 ml
  5. additionof diglyme added
  6. additionfollowed by dropwise addition of 20 g
  7. distillationDiglyme was distilled from the system
  8. temperaturethe resulting mixture heated at 230°-240°C. for 18 hours
  9. additionof ether was added to the cooled mixture
  10. customto remove salts
  11. washThe ethereal solution was washed thoroughly with aqueous base, water
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customThe ether was removed under vacuum
  14. distillationthe resulting oil was distilled
  15. customto give 24.4 g

Sources & evidence

ORD record
ord-a959a54200f24f12818f9508cd420201
Source dataset
uspto-grants-1976_05
Patent number
US03957666

Reaction notes

Loading…