Thionyl Chloride → (2-Chlorophenyl)(4-chlorophenyl)methyl chloride

HRID 2267956

Reaction equation

HRID 2267956 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]([Cl:16])=[CH:12][CH:11]=1)O.S(Cl)([Cl:19])=O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([Cl:19])[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 247332(2-Chlorophenyl)(4-chlorophenyl)methanol

Product 1

HCID 247330(2-Chlorophenyl)(4-chlorophenyl)methyl chlorideYield 102.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A stirred solution of 9.0 grams (0.036 mole) of (2-chlorophenyl)(4-chlorophenyl)methanol in 90 mL of chloroform was cooled to 0° C., and 5.3 mL (0.072 mole) of thionyl chloride was added. Upon completion of the addition the reaction mixture was allowed to warm to ambient temperature, where it stirred for about 18 hours. After this time the reaction mixture was filtered and concentrated under reduced pressure. The filtrate was taken up in hexane and subjected to column chromatography on silica gel with hexane as eluant. The product-containing fractions were combined and concentrated under reduced pressure, yielding 10.0 grams of (2-chlorophenyl)(4-chlorophenyl)methyl chloride. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition the reaction mixture
  2. filtrationAfter this time the reaction mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a81c024108954c3da6b384adb0a4da93
Source dataset
uspto-grants-2001_12
Patent number
USH0002007H1

Linked notes

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