Thionyl Chloride → 4-(4-Phenoxyphenoxy)benzoyl chloride

HRID 1886500Notes

Reaction equation

HRID 1886500 reaction equation
[O:1]([C:8]1[CH:23]=[CH:22][C:11]([O:12][C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:26])=O>CN(C)C=O>[O:1]([C:8]1[CH:23]=[CH:22][C:11]([O:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([Cl:26])=[O:18])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 108521644-(4-Phenoxyphenoxy)benzoic acid

Product 1

HCID 198762164-(4-Phenoxyphenoxy)benzoyl chlorideYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
-15 °C

Procedure

A slurry of 2.30 g (7.52 mmols) of 4-(4-phenoxyphenoxy)benzoic acid, 30 ml of thionyl chloride and 2 drops of N,N-dimethylformamide is refluxed under nitrogen atmosphere for 16 hours. Excess thionyl chloride is distilled off to yield an oil, and 200 ml of anhydrous n-hexane is added. The solution is cooled to -15° C., and the resulting precipitate is filtered and dried under nitrogen atmosphere. The precipitate is dissolved in a minimum volume of hot n-hexane, the solution is filtered, and the filtrate is cooled to -15° C. to yield 1.82 g (66 percent yield of 4-(4-phenoxyphenoxy)benzoyl chloride having a melting point of 85° C. to 89° C. by DSC measurement.

Workup

  1. distillationExcess thionyl chloride is distilled off
  2. customto yield an oil, and 200 ml of anhydrous n-hexane
  3. additionis added
  4. filtrationthe resulting precipitate is filtered
  5. customdried under nitrogen atmosphere
  6. dissolutionThe precipitate is dissolved in a minimum volume of hot n-hexane
  7. filtrationthe solution is filtered
  8. temperaturethe filtrate is cooled to -15° C.

Sources & evidence

ORD record
ord-2d13b4d0ae9f417f975d4d10302b827c
Source dataset
uspto-grants-1992_09
Patent number
US05151489

Reaction notes

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