p-Toluenesulfonic acid monohydrate → HCID 53744755, compound

HRID 2227132Notes

Reaction equation

HRID 2227132 reaction equation
[CH2:1]([C:3]1(O)[CH2:8][CH:7]2[CH2:9][CH:4]1[CH2:5][CH2:6]2)[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH:1](=[C:3]1[CH2:8][CH:7]2[CH2:9][CH:4]1[CH2:5][CH2:6]2)[CH3:2]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 12476588HCID 12476588, compound

Product 1

HCID 53744755HCID 53744755, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 600 ml of benzene was dissolved 125.0 g of 2-ethylbicyclo[2.2.1]heptan-2-ol in endo-form. To the solution was added 8.5 g of p-toluenesulfonic acid monohydrate. This reaction mixture was heated, agitated under reflux for 6 hours while removing water, and subjected to conventional post-treatment. The resulting oily substance was purified by silica gel column chromatography, obtaining 85.9 g of 2-ethylidenebicyclo[2.2.1]heptane. The yield was 78.8%.

Workup

  1. temperatureThis reaction mixture was heated
  2. temperatureunder reflux for 6 hours
  3. customwhile removing water
  4. customThe resulting oily substance was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3ccab0ebdb394579a24cbf80fef387c5
Source dataset
uspto-grants-2002_07
Patent number
US06413695B1

Reaction notes

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