2-Chloroethanol → 1,1'-(3-Chloropropylidene)bis(4-fluorobenzene)

HRID 846679Notes

Reaction equation

HRID 846679 reaction equation
[Cl:1][CH2:2][CH2:3]O.S(=O)(=O)(O)O.[F:10][C:11]1[CH:25]=[CH:24][C:14]([CH:15](O)[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH:15]([C:14]1[CH:24]=[CH:25][C:11]([F:10])=[CH:12][CH:13]=1)[C:16]1[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 1118Sulfuric AcidHCID 1230494,4'-Difluorobenzhydryl alcohol

Product 1

HCID 197832871,1'-(3-Chloropropylidene)bis(4-fluorobenzene)Yield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 29,3 g of 2-chloroethanol in toluene 2 ml of concentrated sulphuric acid were added, after which 50 g of 4,4'-difluorobenzhydrol were added under stirring. The mixture was refluxed for 2 h, cooled and more toluene added. The organic phase was washed successively with water, aqueous sodium carbonate, and water and then dried. The solvent was evaporated to give 65 g of a crude product which was distilled to obtain 57.5 g (89,5%) of [1-(2-chloroethyl)]-bis-(4-fluorophenyl)methane.

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. temperaturecooled
  3. washThe organic phase was washed successively with water, aqueous sodium carbonate, and water
  4. customdried
  5. customThe solvent was evaporated
  6. customto give 65 g of a crude product which
  7. distillationwas distilled

Sources & evidence

ORD record
ord-69815d0dedb3455d8ef520f149052189
Source dataset
uspto-grants-1992_08
Patent number
US05137911

Reaction notes

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