p-Toluenesulfonic acid monohydrate → HCID 72738669, compound

HRID 427227Notes

Reaction equation

HRID 427227 reaction equation
[CH2:1]([C:3]1(O)[CH2:11][CH:10]2[CH2:12][CH:4]1[CH:5]1[CH:9]2[CH2:8][CH2:7][CH2:6]1)[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH:1](=[C:3]1[CH2:11][CH:10]2[CH2:12][CH:4]1[CH:5]1[CH:9]2[CH2:8][CH2:7][CH2:6]1)[CH3:2]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 133868225-Ethyloctahydro-1H-4,7-methanoinden-5-ol

Product 1

HCID 72738669HCID 72738669, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 600 ml of benzene was dissolved 155.0 g of 8-ethyltricyclo[5.2.1.02,6 ]decan-8-ol in endo-form. To the solution was added 8.2 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 105.0 g of 8-ethylidenetricyclo[5.2.1.02,6]decane. The yield was 75.3%.

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-1c5c9c9f3fa34be7aaad006b72a461fd
Source dataset
uspto-grants-2001_11
Patent number
US06312867B1

Reaction notes

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