Hydrochloric Acid → p-(1-Chloroethyl)phenyl 2-thienyl ketone

HRID 258930Notes

Reaction equation

HRID 258930 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Cl:6][CH:7]([C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1)[CH3:8].Cl>C(Cl)Cl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:13]([C:12]1[CH:16]=[CH:17][C:9]([CH:7]([Cl:6])[CH3:8])=[CH:10][CH:11]=1)=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8030ThiopheneHCID 222832114-(1-Chloroethyl)benzoyl chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred and cooled (0° C) mixture of 4.2 parts of thiophene, 13 parts of stannic chloride and 40 parts of methylene chloride is added dropwise a solution of 10.2 parts of p-(1-chloroethyl)benzoyl chloride in 20 parts of methylene chloride (exothermic reaction with gaseous hydrogen chloride evolution). After stirring for 2h. 30 the reaction mixture is poured onto a mixture of crushed ice and hydrochloric acid solution. The product is extracted with methylene chloride. The organic layer is separated, washed with alkaline water, dried and evaporated. The solid residue is triturated with hot petroleum-ether. The product is filtered off and crystallized from ethanol, yielding p-(1-chloroethyl)phenyl 2-thienyl ketone.

Workup

  1. temperaturecooled
  2. stirringAfter stirring for 2h
  3. extractionThe product is extracted with methylene chloride
  4. customThe organic layer is separated
  5. washwashed with alkaline water
  6. customdried
  7. customevaporated
  8. customThe solid residue is triturated with hot petroleum-ether
  9. filtrationThe product is filtered off
  10. customcrystallized from ethanol

Sources & evidence

ORD record
ord-c8cec643ba2540be87bc140452201465
Source dataset
uspto-grants-1977_07
Patent number
US04035376

Reaction notes

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