Hydrochloric Acid → 4-Ethylphenyl 2-thienyl ketone

HRID 258920Notes

Reaction equation

HRID 258920 reaction equation
[CH2:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)[CH3:2].[S:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1.Cl>C(Cl)Cl>[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:7]([C:6]1[CH:10]=[CH:11][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=1)=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8030ThiopheneHCID 853684-Ethylbenzoyl chloride

Product 1

HCID 1043214-Ethylphenyl 2-thienyl ketone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 26.7 parts of p-ethylbenzoyl chloride, 13.3 parts of thiophene in 80 parts of methylene chloride are added 41.1 parts of stannic chloride in 40 parts of methylene chloride at 30° C. Upon completion, stirring is continued for 3h. 30 at reflux temperature. The reaction mixture is poured onto a mixture of crushed ice and hydrochloric acid. The layers are separated and the aqueous phase is extracted with methylene chloride. The combined organic layers are washed with water, dried, filtered and evaporated. The residue is evaporated once more from benzene. The latter residue is distilled, yielding p-ethylphenyl 2-thienyl ketone; bp. 200°-205° C at 12 mm. pressure.

Workup

  1. temperature30 at reflux temperature
  2. customThe layers are separated
  3. extractionthe aqueous phase is extracted with methylene chloride
  4. washThe combined organic layers are washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is evaporated once more from benzene
  9. distillationThe latter residue is distilled

Sources & evidence

ORD record
ord-8dde538cff114009af89d23d37c9eaa2
Source dataset
uspto-grants-1977_07
Patent number
US04035376

Reaction notes

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