p-Toluenesulfonic acid → HCID 86734007, compound

HRID 1576547Notes

Reaction equation

HRID 1576547 reaction equation
C1CO[C:3]2([CH2:7][CH2:6][CH:5]([CH2:8][CH:9]=[O:10])[CH:4]2[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH3:15])[O:2]1.O1CCOCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH:9]([CH2:8][CH:5]1[CH2:6][CH2:7][C:3](=[O:2])[CH:4]1[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH3:15])=[O:10]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 312751,4-DioxaneHCID 86734006HCID 86734006, compound

Product 1

HCID 86734007HCID 86734007, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 47.6 g of 1,1-ethylenedioxy-3-formylmethyl-2-(cis-2-n-pentenyl)-cyclopentane, 80 ml of dioxane, 64 ml of water and 0.38 g para-toluenesulphonic acid is refluxed for 3 hours. It is then cooled, 120 ml of water added and extracted three times with 100 ml of benzene. The benzene solutions are washed to neutrality and concentrated under reduced pressure. There is obtained a crude product which is carefully rectified to yield 18.6 g of pure 3-formylmethyl-2-(cis-2-n-pentenyl)-1-cyclopentanone exhibiting: b.p.0.5 = 96°C. It can be represented by the formula ##SPC24##

Workup

  1. temperatureis refluxed for 3 hours
  2. temperatureIt is then cooled
  3. extractionextracted three times with 100 ml of benzene
  4. washThe benzene solutions are washed to neutrality
  5. concentrationconcentrated under reduced pressure
  6. customThere is obtained a crude product which

Sources & evidence

ORD record
ord-a7a9ebfb59f949d2bdfdf7c00fb34ce0
Source dataset
uspto-grants-1976_09
Patent number
US03981891

Reaction notes

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