Thionyl Chloride → 4'-(Phenylmethoxy)(1,1'-biphenyl)-4-carbonyl chloride

HRID 1722610Notes

Reaction equation

HRID 1722610 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:23])=O)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:26])=O>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([Cl:26])=[O:23])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 147447934'-(Benzyloxy)[1,1'-biphenyl]-4-carboxylic acid

Product 1

HCID 150849044'-(Phenylmethoxy)(1,1'-biphenyl)-4-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

In a 100-ml, three-necked, round-bottomed flask equipped with a magnetic stirrer, an oil bath, and a condenser topped with a drying tube were placed 1.69 g of 4-benzyloxy-4'-biphenylcarboxylic acid, 34 ml of thionyl chloride, and one drop of dimethylformamide. After stirring the solution for three hours under reflux, the thionyl chloride was distilled off, then 75 ml tetrachloromethane was added and distilled. The brown solid was dissolved in 500 ml hot dichloromethane, and the solution was treated with charcoal and filtered through Celite. The solids were washed with hot dichloromethane, and the filtrate was evaporated, to yield the following compound. ##STR26##

Workup

  1. customIn a 100-ml, three-necked, round-bottomed flask equipped with a magnetic stirrer, an oil bath, and a condenser
  2. customtopped with a drying tube
  3. temperatureunder reflux
  4. distillationthe thionyl chloride was distilled off
  5. addition75 ml tetrachloromethane was added
  6. distillationdistilled
  7. dissolutionThe brown solid was dissolved in 500 ml hot dichloromethane
  8. additionthe solution was treated with charcoal
  9. filtrationfiltered through Celite
  10. washThe solids were washed with hot dichloromethane
  11. customthe filtrate was evaporated
  12. customto yield the following compound

Sources & evidence

ORD record
ord-cf8bfbc9c578490b806bf7d4703e8c71
Source dataset
uspto-grants-1989_08
Patent number
US04857227

Reaction notes

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