Thionyl Chloride → p-(1-Chloroethyl)phenyl 2-thienyl ketone

HRID 461736Notes

Reaction equation

HRID 461736 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH:14](O)[CH3:15])=[CH:10][CH:9]=1)=[O:7].S(Cl)([Cl:19])=O>C1C=CC=CC=1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]([Cl:19])[CH3:15])=[CH:10][CH:9]=1)=[O:7]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12232927p-(1-Hydroxyethyl)phenyl 2-thienyl ketone

Product 1

HCID 12232928p-(1-Chloroethyl)phenyl 2-thienyl ketone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred and cooled solution of 43.7 parts of p-(1-hydroxyethyl)phenyl 2-thienyl ketone in 180 parts of dry benzene are added dropwise 16 parts of thionyl chloride. Upon completion, stirring is continued overnight at room temperature. The reaction mixture is evaporated. The residue is taken up in toluene and the latter is evaporated once more. The latter residue is distilled and the distillate is crystallized from ethanol at room temperature, yielding p-(1-chloroethyl)phenyl 2-thienyl ketone; mp. 60° C.

Workup

  1. stirringUpon completion, stirring
  2. customThe reaction mixture is evaporated
  3. customthe latter is evaporated once more
  4. distillationThe latter residue is distilled
  5. customthe distillate is crystallized from ethanol at room temperature

Sources & evidence

ORD record
ord-e836e8cff79f468099b325e1392aaf62
Source dataset
uspto-grants-1977_12
Patent number
US04064132

Reaction notes

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