Pyridine → 4-[[8-[(4-Methylphenyl)sulfonyl]octyl]oxy]-1,1-biphenyl

HRID 256501Notes

Reaction equation

HRID 256501 reaction equation
[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][C:4]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]O)=[CH:3][CH:2]=1.[S:23](Cl)([C:26]1[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=1)(=[O:25])=[O:24].N1C=CC=CC=1>O>[CH3:30][C:29]1[CH:31]=[CH:32][C:26]([S:23]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][O:7][C:4]2[CH:5]=[CH:6][C:1]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:2][CH:3]=2)(=[O:25])=[O:24])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 139591154-(8-Hydroxyoctyl)oxybiphenyl

Product 1

HCID 230435324-[[8-[(4-Methylphenyl)sulfonyl]octyl]oxy]-1,1-biphenyl

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 33.26 g of 8-([1,1'-biphenyl]-4-yl-oxy)-1-octanol, 23.37 g of tosyl chloride and 200 ml of pyridine was allowed to stand in a refrigerator overnight. Then water was added, the solid collected, washed with water and dissolved in chloroform. This solution was washed with dilute hydrochloric acid then saturated aqueous sodium bicarbonate, dried and the solvent removed, giving the desired compound as a white solid.

Workup

  1. customto stand in a refrigerator overnight
  2. customthe solid collected
  3. washwashed with water
  4. dissolutiondissolved in chloroform
  5. washThis solution was washed with dilute hydrochloric acid
  6. dry with materialsaturated aqueous sodium bicarbonate, dried
  7. customthe solvent removed

Sources & evidence

ORD record
ord-fdef6fc129804af98d0c893e93407767
Source dataset
uspto-grants-1987_10
Patent number
US04703130

Reaction notes

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