Selenium Dioxide → HCID 19100279, compound

HRID 1975528Notes

Reaction equation

HRID 1975528 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]([CH3:15])=[CH2:14])[CH:9]=2)[CH:4]=1.[Se](=O)=[O:17]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13](=[CH2:15])[CH2:14][OH:17])[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 5084230Naphthalene, 2-methoxy-6-(1-methylethenyl)-

Product 1

HCID 19100279HCID 19100279, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.20 g 2-methoxy-6-isopropenylnaphthalene and 0.12 g selenium dioxide (SeO2) in 10 ml methylene chloride was heated at reflux for 22 hours. The cooled solution was then washed with 10 ml 20% (by weight) sodium hydroxide (NaOH) after adding 40 ml ethylene dichloride (EDC). The organic layer was dried over MgSO4, filtered, and concentrated to give an oil which was purified on a 2×17 cm silica (SiO2) column using a 5 to 1 by volume solution of heptane and ethyl acetate. The product containing fractions were combined and concentrated to give 2-(6-methoxy-2-naphthyl)prop-2-en-1-ol.

Workup

  1. temperatureat reflux for 22 hours
  2. washThe cooled solution was then washed with 10 ml 20% (by weight) sodium hydroxide (NaOH)
  3. additionafter adding 40 ml ethylene dichloride (EDC)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oil which
  8. customwas purified on a 2×17 cm silica (SiO2) column
  9. additionThe product containing fractions
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d83a64d9f3db4d4eb347e97a49854a78
Source dataset
uspto-grants-1994_02
Patent number
US05286902

Reaction notes

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