Acetic Acid → HCID 12595535, compound

HRID 1448552Notes

Reaction equation

HRID 1448552 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1([C:17]#[N:18])[CH2:11][CH2:10][C:9](=[O:12])[CH:8](C(OC)=O)[CH2:7]1.C(O)(=O)C.S(=O)(=O)(O)O>O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1([C:17]#[N:18])[CH2:7][CH2:8][C:9](=[O:12])[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 12595525HCID 12595525, compound

Product 1

HCID 12595535HCID 12595535, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8.0 g. (0.0304 mole) of 4-(2-thienyl)-4-cyano-2-carbomethoxycyclohexanone in 200 ml. acetic acid and 100 ml. 10% aqueous sulfuric acid is heated on the steam bath with mechanical stirring for 24 hours. The mixture is then allowed to cool, diluted with water and extracted thoroughly with benzene. The organic layer is washed in turn with water, aqueous sodium bicarbonate and brine and taken to dryness. The residual solid is recrystallized from methylene chloride:Skellysolve B to afford 4.10 g. (66% yield) of 4-(2-thienyl)-4-cyanocyclohexanone, m.p. 117.5°-119° C.

Workup

  1. additionA mixture of 8.0 g
  2. temperatureto cool
  3. extractionextracted thoroughly with benzene
  4. washThe organic layer is washed in turn with water, aqueous sodium bicarbonate and brine
  5. customThe residual solid is recrystallized from methylene chloride
  6. customSkellysolve B to afford 4.10 g

Sources & evidence

ORD record
ord-d16eb7b0e9da4a0480db6a9ff1945661
Source dataset
uspto-grants-1979_12
Patent number
US04180584

Reaction notes

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