Thionyl Chloride → HCID 14674270, compound

HRID 1703787Notes

Reaction equation

HRID 1703787 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14](O)[CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:19])=O>C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([Cl:19])[CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20559498HCID 20559498, compound

Product 1

HCID 14674270HCID 14674270, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred suspension of 238 g of 1-(4'-chloro[1,1']biphenyl-4-yl)ethanol in 2 liters of anhydrous benzene add 200 ml. of thionyl chloride over 40 minutes. With stirring, reflux the reaction mixture for 4 hours. Concentrate the reaction mixture and dissolve the resulting solid residue in 2 liters of methylene chloride. Wash the methylene chloride solution with three 500 ml portions of water, dry the resulting solution over sodium sulfate, concentrate, and triturate the solid residue with petroleum ether to yield 4'-chloro-4-(1-chloroethyl)[1,1']-biphenyl m.p. 100°-102° C.

Workup

  1. additionadd 200 ml
  2. temperaturereflux the reaction mixture for 4 hours
  3. concentrationConcentrate the reaction mixture
  4. dissolutiondissolve the resulting solid residue in 2 liters of methylene chloride
  5. washWash the methylene chloride solution with three 500 ml portions of water
  6. dry with materialdry the resulting solution over sodium sulfate
  7. concentrationconcentrate
  8. customtriturate the solid residue with petroleum ether

Sources & evidence

ORD record
ord-b73d9dc36c0c4ac8a56168a0fe12a6f3
Source dataset
uspto-grants-1978_11
Patent number
US04125612

Reaction notes

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