Acetic Acid → 3-Cyclopentene-1-acetaldehyde, 2,2,3-trimethyl-

HRID 1375333Notes

Reaction equation

HRID 1375333 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=C[CH:2]=1.[CH:8](=[O:11])[CH2:9][CH3:10].N1CCCC[CH2:13]1.C(O)(=O)C>O>[CH3:13][C:6]1[C:1]([CH3:2])([CH3:7])[CH:10]([CH2:9][CH:8]=[O:11])[CH2:4][CH:5]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 1140TolueneHCID 8082Piperidine

Product 1

HCID 984973-Cyclopentene-1-acetaldehyde, 2,2,3-trimethyl-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3.04 kg of campholene aldehyde and 2 kg of toluene were introduced into a 10-liter glass reactor and 2.9 kg of propionaldehyde, 170 g of piperidine and 120 g of glacial acetic acid were added with stirring at room temperature. The mixture was then refluxed for 4 hours on a water separator, 680 ml of water of reaction being removed from the circuit. Analysis of a sample of the reaction mixture by gas chromatography revealed a percentage content of 15% of unreacted educt. Accordingly, another 85 g of piperidine and 60 g of glacial acetic acid were added. After refluxing for another hour, another 120 g of water were removed from the circuit and the educt was completely reacted.

Workup

  1. custombeing removed from the circuit
  2. additionAccordingly, another 85 g of piperidine and 60 g of glacial acetic acid were added
  3. temperatureAfter refluxing for another hour
  4. customanother 120 g of water were removed from the circuit
  5. customthe educt was completely reacted

Sources & evidence

ORD record
ord-7c86cd045b0d43c9b2d9b2d7e40b341a
Source dataset
uspto-grants-2007_01
Patent number
US07169749B1

Reaction notes

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