Thionyl Chloride → 4-(4-Phenoxyphenoxy)benzoyl chloride
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -15 °C
Procedure
A slurry of 2.30 (7.52 mmol) g 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 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
- temperatureis refluxed under nitrogen atmosphere for 16 hours
- distillationExcess thionyl chloride is distilled
- customto yield an oil, and 200 ml of anhydrous n-hexane
- additionis added
- filtrationthe resulting precipitate is filtered
- customdried under nitrogen atmosphere
- dissolutionThe precipitate is dissolved in a minimum volume of hot n-hexane
- filtrationthe solution is filtered
- temperaturethe filtrate is cooled to -15° C.
Sources & evidence
- ORD record
- ord-3ee0325d83b94deb95cbacccc1de3fe3
- Source dataset
- uspto-grants-1991_07
- Patent number
- US05030706
Reaction notes
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