Acetic Acid → HCID 575532, compound

HRID 585166Notes

Reaction equation

HRID 585166 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:8]1[CH2:12][CH:11]=[CH:10][CH:9]=1.N1CCCC1.CC(O)=O>CO>[CH2:4]1[CH2:5][CH2:6][C:1](=[C:11]2[CH:10]=[CH:9][CH:8]=[CH:12]2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7612CyclopentadieneHCID 7967CyclohexanoneHCID 31268Pyrrolidine

Product 1

HCID 575532HCID 575532, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7 g of cyclohexanone (71 mmol) and 14.35 ml of cyclopentadiene(175 mmol) were charged in a 300 ml reaction bottle. 70 ml of CH3OH was added as a solvent. Then, 8.75 ml of pyrrolidine (105 mmol) was added gradually and the mixture was stirred at room temperature for 30 minutes. Next, 6.3 ml of CH3COOH (105 mmol) was added gradually and stirred for 10 minutes. 200 ml of H2O and 200 ml of pentane were used for extraction. The upper pentane portion was collected. The lower water portion was further extracted with pentane three times. The collected pentane portion was dehydrated with MgSO4, held still for 30 minutes, filtered, and concentrated under reduced pressure to afford a yellow liquid product (8.7 g, yield=83.3%).

Workup

  1. stirringstirred for 10 minutes
  2. extraction200 ml of H2O and 200 ml of pentane were used for extraction
  3. customThe upper pentane portion was collected
  4. extractionThe lower water portion was further extracted with pentane three times
  5. waitheld still for 30 minutes
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7ca4d62df784fbbb0e9d70039152a2d
Source dataset
uspto-grants-2005_08
Patent number
US06930157B2

Reaction notes

Loading…