Hydrochloric Acid → 4'-Chloro[1,1'-biphenyl]-4-carbaldehyde

HRID 1702538Notes

Reaction equation

HRID 1702538 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2C=CC=CC=2)=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C]=[O:19].Cl.[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)(Cl)(Cl)Cl.O.C(O)=O>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:2]2[CH:7]=[CH:6][C:5]([CH:8]=[O:19])=[CH:4][CH:3]=2)=[CH:24][CH:23]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7964ChlorobenzeneHCID 163234-ChlorobiphenylHCID 6451240Aluminum(III) ChlorideHCID 178418416HCID 178418416, compound

Product 1

HCID 5925704'-Chloro[1,1'-biphenyl]-4-carbaldehyde

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-chlorobiphenyl (18.8 g.) and aluminium chloride (29.5 g.) was stirred in chlorobenzene (150 ml.) at 55°-60° C., in a pressure vessel. The vessel was pressurised to 2 bars with an equimolar mixture of carbon monoxide and hydrogen chloride (prepared by the action of 98-100% formic acid on chlorosulphonic acid). These reaction conditions were maintained for a period of 4 days. After this time the reaction mixture was added, with stirring, to a mixture of ice (500 g.) and water (500 ml.). The organic phase was separated and the aqueous phase was extracted with chlorobenzene (50 ml.). The combined organic phases were then washed successively with 2 M hydrochloric acid (100 ml.) and water (2×100 ml.), and evaporated onto chromotographic silica gel (40 g.). The residue obtained was added to the top of a column of chromatographic silica gel (160 g.) made up in carbon tetrachloride. The column was then washed through with carbon tetrachloride (2000 ml.) and then eluted with chloroform (2000 ml.) The fractions containing material of Rf value (system: SiO2 ; methylene chloride/carbon tetrachloride 1:1 v/v) were combined and evaporated to give 4-(4-chlorophenyl)benzaldehyde (7.3 g.) m.p. 108°-112° C. (after recrystallisation from aqueous acetonitrile).

Workup

  1. customThese reaction conditions
  2. temperaturewere maintained for a period of 4 days
  3. additionAfter this time the reaction mixture was added
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted with chlorobenzene (50 ml.)
  6. washThe combined organic phases were then washed successively with 2 M hydrochloric acid (100 ml.) and water (2×100 ml.)
  7. customevaporated onto chromotographic silica gel (40 g.)
  8. customThe residue obtained
  9. additionwas added to the top of a column of chromatographic silica gel (160 g.)
  10. washThe column was then washed through with carbon tetrachloride (2000 ml.)
  11. washeluted with chloroform (2000 ml.) The fractions
  12. additioncontaining material of Rf value (system: SiO2 ; methylene chloride/carbon tetrachloride 1:1 v/v)
  13. customevaporated

Sources & evidence

ORD record
ord-4e1d22e118f54a91a18d63b071f2d6ef
Source dataset
uspto-grants-1982_09
Patent number
US04348322

Reaction notes

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