Acetic Acid → 2-(1-Benzothiophen-5-yl)-3-methylbutanoic acid

HRID 1758265Notes

Reaction equation

HRID 1758265 reaction equation
[CH:1]([CH:4]([C:7]1[CH:15]=[CH:14][C:10]2[S:11][CH:12]=[CH:13][C:9]=2[CH:8]=1)[C:5]#N)([CH3:3])[CH3:2].S(=O)(=O)(O)[OH:17].C(O)(=O)C.[OH2:25]>>[CH:1]([CH:4]([C:7]1[CH:15]=[CH:14][C:10]2[S:11][CH:12]=[CH:13][C:9]=2[CH:8]=1)[C:5]([OH:17])=[O:25])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962Water2×HCID 1118Sulfuric AcidHCID 20510017alpha-Isopropylbenzo(b)thiophene-5-acetonitrile

Product 1

HCID 205100032-(1-Benzothiophen-5-yl)-3-methylbutanoic acidYield 28.9%

Procedure

A mixture of α-isopropylbenzo(b)thiophene-5-acetonitrile (2.00 g, 0.0093 mol), concentrated sulphuric acid (6.4 cm3), water (6.4 cm3) and acetic acid (26 cm3) was refluxed for 18 hr. The cooled mixture was poured into water and extracted with ether. The ether extract was extracted with saturated sodium bicarbonate solution. The aqueous solution was acidified and extracted with ether. The organic extract was dried (Na2SO4), filtered and the solvent was removed to give α-isopropylbenzo(b)thiophene-5-acetic acid (0.63 g, 2.7 m mol, 28.9%) m.p. 150°-151° C.

Workup

  1. temperaturewas refluxed for 18 hr
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. extractionwas extracted with saturated sodium bicarbonate solution
  5. extractionextracted with ether
  6. extractionThe organic extract
  7. dry with materialwas dried (Na2SO4)
  8. filtrationfiltered
  9. customthe solvent was removed

Sources & evidence

ORD record
ord-dcd7e49303db40c082106e6996c2851e
Source dataset
uspto-grants-1983_02
Patent number
US04372970

Reaction notes

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