Thionyl Chloride → alpha-Chloro-p-tolyl 2-thienyl ketone

HRID 1439558

Reaction equation

HRID 1439558 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]([CH2:14]O)=[CH:10][CH:9]=1)=[O:7].S(Cl)([Cl:18])=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]([CH2:14][Cl:18])=[CH:10][CH:9]=1)=[O:7]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21391792alpha-Hydroxy-p-tolyl 2-thienyl ketone

Product 1

HCID 21391736alpha-Chloro-p-tolyl 2-thienyl ketone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred and cooled suspension of 31 parts of α-hydroxy-p-tolyl 2-thienyl ketone in 160 parts of dry benzene are added dropwise 24 parts of thionyl chloride at 10° C. Upon completion, stirring is continued overnight at room temperature. The reaction mixture is evaporated and the residue is evaporated twice more from toluene. The latter residue is triturated in petroleumether. The product is filtered off and dissolved in 320 parts of ether. This solution is stirred with charcoal, filtered and the filtrate is evaporated. The residue is crystallized from ethanol at -20° C, yielding α-chloro-p-tolyl 2-thienyl ketone.

Workup

  1. temperaturecooled
  2. stirringUpon completion, stirring
  3. customThe reaction mixture is evaporated
  4. customthe residue is evaporated twice more from toluene
  5. customThe latter residue is triturated in petroleumether
  6. filtrationThe product is filtered off
  7. dissolutiondissolved in 320 parts of ether
  8. stirringThis solution is stirred with charcoal
  9. filtrationfiltered
  10. customthe filtrate is evaporated
  11. customThe residue is crystallized from ethanol at -20° C

Sources & evidence

ORD record
ord-6f9f240ca6b442e68d5674a0bf10a51c
Source dataset
uspto-grants-1977_11
Patent number
US04060528

Linked notes

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