p-Toluenesulfonic acid → HCID 20473493, compound

HRID 2296069Notes

Reaction equation

HRID 2296069 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[CH:8]=[O:9].[CH:10]12[CH2:16][CH:13]([CH:14]=[CH:15]1)[CH2:12][CH:11]2[CH2:17][OH:18].[C:19]1([CH3:29])[CH:24]=[CH:23][C:22](S(O)(=O)=O)=[CH:21][CH:20]=1.N1C2C(=CC=CC=2)C=C[CH:31]=1>C1CCCCC1>[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[CH2:8][O:9][CH:17]([O:18][CH2:29][CH:19]1[CH2:24][CH:23]2[CH2:31][CH:20]1[CH:21]=[CH:22]2)[CH:11]1[CH2:12][CH:13]2[CH2:16][CH:10]1[CH:15]=[CH:14]2

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 7047QuinolineHCID 78946Bicyclo(2.2.1)hept-5-ene-2-methanolHCID 95117Bicyclo(2.2.1)hept-5-ene-2-carboxaldehyde

Product 1

HCID 20473493HCID 20473493, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

122 g (1 mole) of bicyclo-[2,2,1]-hept-5-en-2-aldehyde and 248 g (2 moles) of bicyclo-[2,2,1]-hept-5-en-2-yl-methyl alcohol are dissolved in 600 ml of cyclohexane. A mixture of 3.5 g of p-toluene sulfonic acid and 2.6 g of quinoline are added to the resulting solution which is then boiled on a water separator until the removal of water has ceased. The product is then carefully washed until it shows a neutral reaction, dried with potassium carbonate and distilled. A colourless oil is obtained, solidifying into a wax-like substance.

Workup

  1. additionare added to the resulting solution which
  2. customis then boiled on a water separator until the removal of water
  3. washThe product is then carefully washed until it
  4. customa neutral reaction
  5. dry with materialdried with potassium carbonate
  6. distillationdistilled
  7. customA colourless oil is obtained

Sources & evidence

ORD record
ord-59d7935313264703ab526803d9f8ab60
Source dataset
uspto-grants-1984_01
Patent number
US04427817

Reaction notes

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