HCID 14537117, compound → HCID 14537119, compound

HRID 2165194Notes

Reaction equation

HRID 2165194 reaction equation
[OH:1][CH2:2][C:3]#[C:4][CH2:5][CH2:6][CH2:7][C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[CH:23]=[C:22]([O:24]C)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]=1[OH:26]>C(#N)C.O.C(#N)C.O>[OH:1][CH2:2][C:3]#[C:4][CH2:5][CH2:6][CH2:7][C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[C:15](=[O:26])[C:16]2[C:21]([C:22](=[O:24])[CH:23]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2

Participants

5

Reactant 1

HCID 14537117HCID 14537117, compound

Product 1

HCID 14537119HCID 14537119, compoundYield 98.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

2-(12-Hydroxydodeca-5,10-diynyl)-1-hydroxy-4-methoxynaphthalene (80 mg) is dissolved in 1 ml of acetonitrile and 0.75 ml of water. This mixture is cooled in an ice bath and the addition of ceric ammonium nitrate (0.377 g) in 2 ml of 50% acetonitrile/water is carried out over 10 minutes. Stirring is continued an additional 30 minutes (after only 5 minutes a yellow precipitate forms). The above contents are poured into a separatory funnel and additional water is added. The mixture is extracted three times with methylene chloride and the combined organic extracts are washed with water, saturated sodium bicarbonate, and brine, dried with magnesium sulfate, filtered, and concentrated to provide 74.9 mg of the title compound as a yellow solid, mp 88°-89.5° C. By TLC (in 2% acetone/methylene chloride) the material is fairly clean, with a small amount of impurities at lower Rf. Drying the sample under low vacuum (0.2 mm) overnight changes the melting point slightly, mp 89°-90.5° C.

Workup

  1. temperatureThis mixture is cooled in an ice bath
  2. waitis continued an additional 30 minutes
  3. wait(after only 5 minutes a yellow precipitate forms)
  4. additionThe above contents are poured into a separatory funnel
  5. extractionThe mixture is extracted three times with methylene chloride
  6. washthe combined organic extracts are washed with water, saturated sodium bicarbonate, and brine
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-50da7c6dc04147bba78acf8ea2e8cf88
Source dataset
uspto-grants-1990_07
Patent number
US04939169

Reaction notes

Loading…