Acetic Acid → HCID 12439129, compound

HRID 2052223Notes

Reaction equation

HRID 2052223 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH2:10][CH2:11]C2C#N)=[O:7].S(=O)(=O)(O)O.[C:24]([OH:27])(=[O:26])[CH3:25]>O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH2:10][CH2:11][CH:25]2[C:24]([OH:27])=[O:26])=[O:7]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 12439126HCID 12439126, compound

Product 1

HCID 12439129HCID 12439129, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2.5 g of 4-(2-thienylcarbonyl)-1-indancarbonitrile is added 20 ml of 60% sulfuric acid together with 10 ml of acetic acid. The mixture is refluxed in argon gas for 2.5 hours. After cooling, water is added to the reaction mixture which is then extracted with benzene. The benzene layer is washed with water and extracted with a 5% aqueous solution of potassium carbonate. The extract is made acidic with hydrochloric acid and the precipitate is extracted with benzene. The benzene layer is washed with water, dried and decolorized with activated carbon. The solvent is then distilled off under reduced pressure and the residue is crystallized from benzene-cyclohexane (1:2). By the above procedure is obtained 4-(2-thienylcarbonyl)-1-indancarboxylic acid as crystals melting at 121.5°-123.5° C.

Workup

  1. temperatureThe mixture is refluxed in argon gas for 2.5 hours
  2. temperatureAfter cooling
  3. extractionis then extracted with benzene
  4. washThe benzene layer is washed with water
  5. extractionextracted with a 5% aqueous solution of potassium carbonate
  6. extractionthe precipitate is extracted with benzene
  7. washThe benzene layer is washed with water
  8. customdried
  9. distillationThe solvent is then distilled off under reduced pressure
  10. customthe residue is crystallized from benzene-cyclohexane (1:2)

Sources & evidence

ORD record
ord-affc344824104960a50404963640f6ff
Source dataset
uspto-grants-1980_01
Patent number
US04183859

Reaction notes

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