Thionyl Chloride → 4-Phenylbenzoyl chloride

HRID 2052143Notes

Reaction equation

HRID 2052143 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([C:7](O)=[O:8])=[CH:3][CH:2]=1.S(Cl)([Cl:18])=O>>[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([C:7]([Cl:18])=[O:8])=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 66724(1,1'-Biphenyl)-4-carboxylic acid

Product 1

HCID 841514-Phenylbenzoyl chloride

Procedure

Heated at reflux for 2 hrs., a solution of 25 g (0.13 mole) of 4-biphenylcarboxylic acid, in 125 ml of thionyl chloride. Distilled to remove the excess thionyl chloride, then added 150 ml of AR toluene. Evaporated in vacuo to give a brown solid, 27 g, m.p. softens 107°, some melts 109°-112°, darkens 370°, melts >400°.

Workup

  1. temperatureHeated
  2. temperatureat reflux for 2 hrs
  3. distillationDistilled
  4. customto remove the excess thionyl chloride
  5. additionadded 150 ml of AR toluene
  6. customEvaporated in vacuo
  7. customto give a brown solid, 27 g
  8. customm.p. softens 107°
  9. customsome melts 109°-112°
  10. customdarkens 370°
  11. custommelts >400°

Sources & evidence

ORD record
ord-a0e81581833540fb8d76c1c3cd1e00e7
Source dataset
uspto-grants-1980_01
Patent number
US04182881

Reaction notes

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