p-Toluenesulfonic acid → HCID 21511384, compound

HRID 1576544Notes

Reaction equation

HRID 1576544 reaction equation
C1CO[C:3]2([CH2:7][CH2:6][CH:5]([CH2:8][CH:9]=[O:10])[CH:4]2[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[O:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O1CCOC1.C1COC2C(C(C)(CCCCC)C(=O)C2)O1>O.O1CCOCC1>[CH:9]([CH2:8][CH:5]1[CH2:6][CH2:7][C:3](=[O:2])[CH:4]1[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:10]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 125861,3-DioxolaneHCID 21511377HCID 21511377, compoundHCID 68140586HCID 68140586, compound

Product 1

HCID 21511384HCID 21511384, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 24 g of 1,1-ethylenedioxy-3-formylmethyl-2-n-pentyl-cyclopentane, 40 ml of dioxane, 32 ml of water and 0.18 g paratoluenesulphonic 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 are obtained 22 g of crude product which are rectified and which yield 15.5 g of product; b.p.1.0 = 110°-140°C. The distillate is a mixture of keto aldehyde and the dioxolane of the aldehyde function (3-ethylenedioxymethyl-2-n-pentyl-1-cyclopentanone) in the proportions of 75/25. By careful rectification of this mixture, there is obtained 11 g of pure 3-formylmethyl-2-n-pentyl-1-cyclopentanone exhibiting: b.p.0.5 = 90°C, nD15 = 1.4688.

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 are obtained 22 g of crude product which
  7. customb.p.1.0 = 110°-140°C

Sources & evidence

ORD record
ord-40d0f8e8468943a895409df1c08f5859
Source dataset
uspto-grants-1976_09
Patent number
US03981891

Reaction notes

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