Thionyl Chloride → HCID 22767075, compound

HRID 1111659Notes

Reaction equation

HRID 1111659 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)O.S(Cl)([Cl:24])=O>C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[Cl:24]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 2793934HCID 2793934, compound

Product 1

HCID 22767075HCID 22767075, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

290 g (0.985 mol) of 2-chlorophenyl-(biphenyl-4-yl)-carbinol are dissolved in 1,000 ml of benzene and a solution of 144 ml (2 mols) of thionyl chloride in 400 ml of benzene is added slowly at 40° C. with stirring. The reaction mixture is heated under reflux for 15 hours. The solvent is distilled off in vacuo and the residue is stirred with 500 ml of petroleum ether. The crystals produced are filtered off and purified by recrystallization from ethanol. 36 g (89% of theory) of (2-chlorophenyl)-(biphenyl-4-yl)-chloromethane [alternatively named as α-(biphenyl-4-yl)-2l -chlorobenzyl chloride] of melting point 80° C. are obtained.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 15 hours
  3. distillationThe solvent is distilled off in vacuo
  4. stirringthe residue is stirred with 500 ml of petroleum ether
  5. customThe crystals produced
  6. filtrationare filtered off
  7. custompurified by recrystallization from ethanol
  8. customare obtained

Sources & evidence

ORD record
ord-94f4803919aa46d0bdb97661df228760
Source dataset
uspto-grants-1978_10
Patent number
US04118487

Reaction notes

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